☆ 4.7 Review

Recent Advances in Nucleophilic Lewis Base-Catalyzed Cycloadditions for Synthesis of Spirooxindoles

ADVANCED SYNTHESIS & CATALYSIS (2023)

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Article Chemistry, Organic

Cooperative Tertiary Amine/Palladium-Catalyzed Sequential [4+3] Cyclization/[1,3]-Rearrangement for Stereoselective Synthesis of Spiro [Methylenecyclopentane-1,3′-oxindolines]

Yue-You Chen et al.

Summary: A cooperative tertiary amine/palladium-catalyzed sequential reaction process has been developed for the synthesis of spiro[methylene cyclopentane-1,3 '-oxindo-lines]. This process involves a [4 + 3] cyclization of isatin-derived Morita-Baylis-Hillman Expansion (MBH) carbonates and tert-butyl 2-(hydroxymethyl)allyl carbonates, followed by a [1,3]-rearrangement. The synthetic compounds obtained exhibit excellent regio- and stereocontrol, and this protocol has potential for large-scale synthesis and diverse functional transformations.

JOURNAL OF ORGANIC CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Mechanism of powdered activated carbon enhancing caproate production

Siying Xiang et al.

Summary: Caproate, which can be produced through microbial chain elongation, shows great potential as a carbon-neutral alternative to fossil-based products. However, its production performance needs improvement for industrial applications. This study found that the addition of powdered activated carbon (PAC) significantly enhanced the production, yield, and selectivity of caproate. PAC promoted ethanol oxidation and improved the efficiency of the reverse beta oxidation (RBO) pathway, leading to increased caproate synthesis. Additionally, PAC affected the microbial community, enriching caproate-producing bacteria and eliminating irrelevant ones. Metagenomic analysis revealed that PAC up-regulated key enzyme-encoding genes responsible for ethanol oxidation and RBO pathway, thus improving caproate production. This study provides insights into the mechanism of PAC promotion of caproate generation, laying the foundation for large-scale production of caproate.

CHINESE CHEMICAL LETTERS (2023)

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Article Chemistry, Multidisciplinary

Recent advances in annulations enabled by nucleophilic Lewis base/metal dual catalysis

Qian Wang et al.

Summary: Metal/nucleophilic Lewis base dual catalysis has been recognized as a reliable and promising strategy for finishing ideal organic synthesis. This new strategy expands the synthetic utility of chemical transformations by leveraging additional activation modes and has made considerable progress in the synthesis of a wide range of heterocyclic and biologically active compounds. In this review, the comprehensive and updated advances of metal/nucleophilic Lewis base dual catalytic annulation reactions are described, along with the highlighting of the related mechanism and application in natural product total synthesis.

CHINESE CHEMICAL LETTERS (2023)

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Article Chemistry, Multidisciplinary

Diastereodivergent Desymmetric Annulation to Access Spirooxindoles: Chemical Probes for Mitosis

Yu-Hua Wen et al.

Summary: In this study, a unique catalytic synthesis method was reported, which involved diastereodivergent [3 + 3] annulation of oxabicyclic alkenes with enals enabled by N-heterocyclic carbene (NHC)/Rh cooperative catalysis. Enantiomerically enriched spirooxindole lactones were obtained with excellent enantioselectivities and diastereoselectivities. These compounds showed significant effects on cell division and exhibited potent antiproliferative activities against HeLa cells. The absolute and relative configurations of the stereoisomers also played a crucial role in their bioactivities, highlighting the importance of catalytic asymmetric diastereodivergent synthesis in exploring structure-activity relationships.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

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Article Chemistry, Medicinal

Lewis base-catalyzed synthesis of highly functionalized spirooxindole-pyranopyrazoles and their in vitro anticancer studies

Mohd Asif et al.

Summary: This study reports a series of spirooxindole-pyranopyrazole derivatives synthesized via a one-step, multi-component reaction. The newly synthesized derivatives were screened for in vitro anti-cancer activity at NCI and showed good activity against several cancer cell lines.

MEDICINAL CHEMISTRY RESEARCH (2023)

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Article Chemistry, Multidisciplinary

Chiral NHC-Catalyzed [4+2] Cycloadditions: Highly Diastereo/Enantioselective Access to Spiro[cyclohex-4-ene-1,3' -indoles] and DFT Calculations

Xiaoyu Chen et al.

Summary: A highly efficient NHC-catalyzed cycloaddition of (E)-alkenylisatins and gamma-chloroenals has been developed, providing spiro[cyclohex-4-ene-1,3'-indole] in good yields (up to 99%) with excellent diastereoselectivities and enantioselectivities (up to > 20:1 d.r., > 99% ee) under mild conditions without the use of metals or additives. The role of NHC in the diastereo- and enantioselectivity is discussed based on computational investigations.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

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Article Chemistry, Multidisciplinary

Copper-catalyzed 1,4-protosilylation and 1,4-protoborylation of enynic orthoesters for synthesis of functionalized 2,3-allenoates

Qi Li et al.

Summary: Copper-catalyzed 1,4-protosilylation and 1,4-protoborylation reactions of enynic orthoesters were developed. The enynic orthoesters, as precursors of unstable enynic esters, were used to produce functionalized 2,3-allenoate products. The asymmetric 1,4-protosilylation of enynic orthoesters with PhMe2Si-Bpin was also studied, and the chiral monopyridine imidazoline ligand exhibited high enantioselectivity.

CHINESE CHEMICAL LETTERS (2023)

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Article

Cooperative Dual Organocatalytic Asymmetric Decarboxylative [4 + 3] Annulations with Benzoxazinanones

Ling Zhu et al.

Precision Chemistry (2023)

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Review Chemistry, Multidisciplinary

Recent Advances in Lewis Base-Catalysed Chemo-, Diastereo- and Enantiodivergent Reactions of Electron-deficient Olefins and Alkynes

Yinggao Meng et al.

Summary: Lewis base catalysis provides powerful synthetic strategies for the selective construction of carbon-carbon and carbon-heteroatom bonds. The nucleophilicity and steric hindrance of Lewis base catalyst often plays a major role in catalytic reactivity and selectivity in the reaction. Tremendous progress has been made in the divergent construction of valuable motifs under Lewis base catalysis in the past decades.

CHEMICAL RECORD (2022)

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Article Chemistry, Multidisciplinary

Recent advances in tertiary amine Lewis base-promoted cycloadditions of allenoates

Manman Song et al.

Summary: This review provides a comprehensive and updated summary of the use of tertiary amine Lewis bases as catalysts for annulation reactions of allenoates. The review highlights diverse reactivities, chemoselectivities, and detailed reaction mechanisms.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Applied

Palladium-Catalyzed [4+2] Cycloaddition of Hydroxy-Tethered Allylic Carbonates with Alkenes: Synthesis of Functionalized Tetrahydropyrans

Jiaqing Xu et al.

Summary: A palladium-catalyzed [4+2] cycloaddition reaction has been developed for the efficient synthesis of tetrahydropyran derivatives with good selectivity.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Azulenoisoindigo: A building block for π-functional materials with reversible redox behavior and proton responsiveness

Bin Hou et al.

Summary: In this study, an azulene-based isoindigo analogue, AzII, was designed and synthesized, which exhibited a unique molecular structure and properties. AzII showed characteristics of both isoindigo and azulene, and the possible mechanism of its proton-responsive property was revealed through experimental measurements.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Direct access to spirooxindole dihydropyrrole fused pyrazolones and bis-spiropyrazolone derivatives

Prakash K. Warghude et al.

Summary: A highly selective [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins/pyrazolones with pyrazolone derived ketimines has been developed to access spiroheterocycles. The method efficiently constructs spirooxindole dihydropyrrole fused pyrazolone and bis-spiropyrazolone dihydropyrrole derivatives bearing two vicinal quaternary spirocentres in good to excellent yields with high diastereoselectivities under mild catalytic condition at room temperature. The study demonstrates the utility of DMAP as a commercially viable catalyst for this transformation.

TETRAHEDRON LETTERS (2022)

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Article Chemistry, Physical

Design and Application of Chiral Bifunctional 4-Pyrrolidinopyridines: Powerful Catalysts for Asymmetric Cycloaddition of Allylic N-Ylide

Qingqing Luo et al.

Summary: The study focuses on the design of bifunctional 4-pyrrolidinopyridines as Lewis base catalysts, which exhibited excellent efficiency and stereoselectivity in asymmetric cycloaddition reactions. The research provides strong support for the construction of chiral spiropyrazolone derivatives.

ACS CATALYSIS (2022)

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Article Chemistry, Organic

Rigid P-Chiral Phosphorus Ligands for Highly Selective Palladium- Catalyzed (4+2) and (4+4) Annulations

Yinggao Meng et al.

Summary: We developed novel shackled P-chiral ligands for palladium-catalyzed (4+2) annulations, producing enantioenriched tetrahydropyran scaffolds with high site selectivity and enantioselectivity. Moreover, chemoselective (4+4) products were also achieved using acyclic imines. Density functional theory calculations indicated that the reactions were mostly under thermodynamic control.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3-indolines]

Hui Zheng et al.

Summary: In this study, a reaction system catalyzed by tri(n-butyl)phosphine was developed for the synthesis of functionalized spiro[cyclohexane-1,3'-indolines]. The reaction showed good yields and excellent diastereoselectivity, and the regioselectivity of the products varied with different reactants.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Asymmetric α-Regioselective [3+2] Annulation of Morita-Baylis-Hillman Carbonates: Construction of Three Contiguous Stereocenters with Vicinal Quaternary Carbon Centers

Xiaochen Tian et al.

Summary: The asymmetric alpha-regioselective annulation of MBH carbonates with 4-arylmethylisoxazol-S-ones has been developed, resulting in the synthesis of spirocyclic oxindole derivatives with three contiguous stereogenic centers and vicinal all-carbon quaternary chiral centers. This reaction exhibits a broad substrate scope and excellent functional group tolerance, producing high yields with high diastereo- and enantioselectivities.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Synthesis of Chromone-Spiroindolinone-Cyclopentene Derivatives through Phosphine-Catalyzed (3+2) Annulation of Morita-Baylis-Hillman Carbonates with Oxindole-Chromones

Bo Wang et al.

Summary: Various multifunctional chromone-spiroindolinone-cyclopentene derivatives were synthesized through a phosphine-catalyzed reaction, showing excellent diastereoselectivities and potential application in the synthesis of biologically important compounds.

CHEMISTRYSELECT (2022)

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Article Chemistry, Organic

N-Heterocyclic Carbene-Catalyzed [3+2] Annulation of 3,3'- Bisoxindoles with a-Bromoenals: Enantioselective Construction of Contiguous Quaternary Stereocenters

Binghao Liu et al.

Summary: A new enantio- and diastereoselective reaction has been developed for the synthesis of various spirocyclic bisoxindole alkaloids. This reaction exhibits a broad substrate scope and excellent enantioselectivity, and allows for the creation of two contiguous sterically congested all-carbon quaternary stereocenters.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

4-Dimethylaminopyridine-catalyzed [3+3] spiroannulation reactions of isatin-derived Morita-Baylis-Hillman carbonates with indoline-2-thiones

Congcong Geng et al.

Summary: A series of bisindole-annulated thiopyran frameworks were synthesized with good yields and diastereoselectivities through DMAP-catalyzed reactions, offering a novel synthetic strategy for valuable indole-annulated sulfur heterocycle derivatives, which may have potential applications in organic synthesis and medicinal chemistry.

TETRAHEDRON LETTERS (2022)

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Article Chemistry, Applied

Divergent Reaction of Allenoates: Synthesis of Polysubstituted Pyrazoles and N-Alkylated Hydrazones

Saideh Rajai-Daryasarei et al.

Summary: A strategy for the divergent synthesis of polysubstituted pyrazoles and N-alkylated hydrazone derivatives through a three-component reaction of aromatic aldehydes, aryl sulfonyl hydrazides, and allenoates under mild reaction conditions is described. Both products can be obtained by changing the reaction base.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Organic

The N-heterocyclic carbene-catalyzed [3+2] annulation of isoindigos with enals: the enantioselective construction of three contiguous stereogenic centers

Binghao Liu et al.

Summary: In this work, an efficient strategy for the construction of dimeric spirocyclic bisindoline alkaloid derivatives was introduced using NHC-catalyzed enantioselective [3 + 2] annulation of enals with isoindigo. The reaction successfully constructs three contiguous stereogenic centers, including two congested all-carbon quaternary stereogenic centers, in a simple one-step operation.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Organic

Cooperative palladium-catalyzed P(NEt2)3-mediated (4+1) annulation of isatins with 2 hydroxymethylallylcarbonates

Zhipeng Zhang et al.

Summary: The study achieved (4 + 1) annulations of isatin derivatives with [2-(hydroxymethyl)allyl] carbonates using a cooperative palladium/P(NEt2)(3) system, leading to an extensive library of highly structurally diverse spirooxindole derivatives.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Multidisciplinary

Catalytic asymmetric [3+2] cycloaddition of pyrazolone-derived MBH carbonate: highly stereoselective construction of the bispiro-[pyrazolone-dihydropyrrole-oxindole] skeleton

Zhou Tian et al.

Summary: The catalytic asymmetric construction of the bispiro[pyrazolone-dihydropyrrole-oxindole] skeleton was successfully achieved using a chiral DMAP-derived catalyst and recently explored pyrazolone-derived MBH carbonate. The reaction exhibited high yields and excellent stereoselectivities, with intermolecular hydrogen bonds and pi-pi interactive forces playing a crucial role in the stereoselective chemical transformation.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

Asymmetric Carbene-Catalyzed Oxidation of Functionalized Aldimines as 1,4-Dipoles

Guanjie Wang et al.

Summary: Functionalized aldimines have been used as new 1,4-dipole precursors in carbene catalysis, leading to enantiodivergent organocatalysis for the synthesis of both (R)- and (S)- enantiomers of compounds with quaternary carbon centers. The key factors for controlling enantioselectivity were found to be hydrogen bond C-H...F interactions between catalyst and substrate. These new 1,4-dipoles can also react with isatin and its imines under carbene catalysis, producing spiro oxindoles with excellent enantiomeric ratios.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Kinetic Resolution of Aziridines Enabled by N-Heterocyclic Carbene/Copper Cooperative Catalysis: Carbene Dose-Controlled Chemo-Switchability

Zi-Jing Zhang et al.

Summary: The study developed an efficient KR and DyKAT method using N-heterocyclic carbene (NHC)/copper cooperative catalysis, resulting in highly enantioenriched derivatives and products with high structural diversity. Mechanistic studies indicated that NHC can regulate the catalytic activity of the copper catalyst, enabling the switch of chemical selectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Discovery of spirooxindole-ferrocene hybrids as novel MDM2 inhibitors

Jun Mu et al.

Summary: A series of spirooxindole-ferrocene hybrids with five or four contiguous chiral centers were designed and synthesized through organocatalysis. Compound 5d was identified as the most potent MDM2 inhibitor, suppressing MDM2-mediated p53 degradation, inducing apoptosis, and promoting oxidative damage. Molecular docking studies have shown that 5d binds to MDM2 by mimicking the Trp23 and Leu26 residues of p53, providing a basis for the development of novel multifunctional MDM2 inhibitors.

CHINESE CHEMICAL LETTERS (2021)

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Article Chemistry, Organic

N-Heterocyclic Carbene Catalyzed [3+2] Annulations of β-Halocycloenals with Isatins and Mechanism Study

Gang Wang et al.

Summary: A NHC-catalyzed [3+2] annulation of beta-halocycloenals with isatins upon a dual-activation mode was developed for the synthesis of tetracyclic 3-spirooxindoles, and DFT calculations were performed to study the mechanism of this transformation.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

NHC-catalysed retro-aldol/aldol cascade reaction enabling solvent-controlled stereodivergent synthesis of spirooxindoles

Haijun Leng et al.

Summary: The N-heterocyclic carbene-catalysed retro-aldol/aldol cascade reaction allows for the synthesis of spirocyclopentaneoxindole products with four consecutive stereocenters. By simply changing reaction solvents, diastereodivergent synthesis can be achieved. Selective provision of four stereoisomers can be achieved by using different combinations of a chiral secondary amine and a solvent.

CHINESE CHEMICAL LETTERS (2021)

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Article Chemistry, Organic

Asymmetric [4+3] Annulations for Constructing Divergent Oxepane Frameworks via Cooperative Tertiary Amine/Transition Metal Catalysis

Zhi Chen et al.

Summary: Asymmetric [4 + 3] annulations were successfully achieved using isatin-derived Morita-Baylis-Hillman carbonates and two types of vinyl carbonates synergistically catalyzed by tertiary amines and transition metals. This method allows for the construction of a variety of oxepane frameworks with high stereocontrol, and all four diastereomers for products bearing vicinal stereocenters can be accessed by tuning the tertiary amine and metal catalysts.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Mechanism and selectivity of nickel-catalyzed [3+2] cycloaddition of cyclopropenones and α,β-unsaturated ketones: A computational study

Lingling Liu et al.

Summary: Density functional theory calculations were used to investigate the nickel-catalyzed [3 + 2] cycloaddition reaction, revealing four major steps in the catalytic cycle. The enantioselectivity is mainly determined by the interaction between different groups, while the chemoselectivity can be rationalized in terms of steric effects.

CHINESE CHEMICAL LETTERS (2021)

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Review Chemistry, Organic

Asymmetric Organocatalytic Synthesis of aza-Spirocyclic Compounds from Isothiocyanates and Isocyanides

Adrian Lavios et al.

Summary: The spirocyclic motif is widely found in natural products, chiral ligands, and pharmacologically active compounds. The formal [3+2] cycloaddition reaction of isothiocyanates or isocyanides with cyclic compounds has been developed for the enantioselective synthesis of aza-spirocyclic compounds, with organocatalysis playing a key role in these reactions. The synthesis of spirooxindoles using this methodology has received particular attention, highlighting the importance of the structure of the dipolarophiles and the isothiocyanate and isocyanide dipoles.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Diastereodivergent synthesis of fully disubstituted spiro[indoline-3,2′-pyrrolidin]-2-ones via tuneable Lewis base/Bronsted base-promoted (3+2) cycloadditions

Ke Li et al.

Summary: In this study, a diastereodivergent synthesis of fully disubstituted spiro[indoline-3,2'-pyrrolidin]-2-ones was achieved through base-promoted (3 + 2) cycloadditions. Catalysts were found to exert full control over the configuration of stereocenters. Different diastereoisomers of spiro[indoline-3,2'-pyrrolidin]-2-ones were obtained with good yields by using different types of bases (Lewis base PCy3 and Bronsted base K2CO3), demonstrating the influence of the catalysts on the stereoselectivity of the reaction. ESI-MS experiments confirmed the presence of key zwitterionic intermediates.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

Design of 1-Phosphanorbornene Derivatives as Chiral Organocatalysts for Enantioselective (4+2) Annulation Reactions of γ-Benzyl Allenoates

Siming Jia et al.

Summary: Two novel diastereoisomeric P-chirogenic phosphine catalysts, JiaPhos, were successfully synthesized from inexpensive starting materials in five chemical operations on a 4.16g scale. These catalysts demonstrated excellent performance in enantioselective (4 + 2) annulations, providing a diverse range of 3,3'-spirocyclic oxindoles with high efficiency and enantioselectivity.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Phosphorus-Based Catalysis

Changmin Xie et al.

Summary: Phosphorus-based organocatalysis has experienced rapid growth in recent years, with key advances in nucleophilic phosphine catalysis, organophosphorus catalysis to bypass waste, and organophosphorus compound-mediated single electron transfer processes. Additionally, chiral phosphoric acid catalysis, phosphine oxide Lewis base catalysis, and other topics have been briefly summarized.

ACS CENTRAL SCIENCE (2021)

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Article Chemistry, Applied

One-Pot Construction of Diverse Products using Versatile Cyclopropenones

Tianle Huang et al.

Summary: The tunable C-H activation cascade reactions between quinazolinones and cyclopropenones have been shown to construct various heterocyclic scaffolds, with cyclopropenones acting as multi-functional building blocks in the process.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Review Biochemistry & Molecular Biology

Natural spirocyclic alkaloids and polyphenols as multi target dementia leads

Helmut M. Hugel et al.

Summary: Various plant constituents and fungal extracts contain neuroprotective properties that can combat cytotoxicity. Research on spirocyclic alkaloids may lead to advancements in biotechnological generation, stimulating neurocognitive activities.

BIOORGANIC & MEDICINAL CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Organocatalytic Strategies for the Development of the Enantioselective Inverse-electron-demand Hetero-Diels-Alder Reaction

Victor Laina-Martin et al.

Summary: Cycloaddition reactions, particularly Diels-Alder reactions, are regarded as powerful methodologies for building carbon-carbon bonds. The inverse-electron-demand hetero-Diels-Alder reactions have been a significant breakthrough for synthesizing heterocyclic compounds. Among them, the organocatalytic enantioselective version has been extensively studied due to its asymmetric construction of diversely functionalized scaffolds under green chemistry conditions.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Organic

Catalyst-Controlled Diastereoselectivity Switch in the Asymmetric [3+2] Annulation of Isatin-Derived MBH Carbonates and 5-Alkenyithiazol-4(5H)-ones

Ming-Shun Mei et al.

Summary: The exploration of diastereodivergent synthesis of spirocyclic oxindoles has been challenging, but has been successfully achieved through asymmetric [3+2] annulations using two different chiral catalysts, resulting in two kinds of diastereomeric dispiro oxindoles with three contiguous stereogenic centers. The hexafluoroisopropanol (HFIP) additive plays a crucial role in accelerating the reaction and tuning diastereoselectivity. Moreover, the annulation adducts can be further converted to structurally diverse spirooxindoles.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Phosphine-catalyzed enantioselective [4+1] annulation of oxindoles with allenic ketones for the construction of spirocyclopentene oxindoles

Xiaodong Tang et al.

Summary: The phosphine-catalyzed enantioselective [4 + 1] annulation between allenic ketones and oxindoles produces 3-spirocyclopentene-2-oxindoles with quaternary stereogenic centers in high yields and excellent enantioselectivities. The synthetic elaborations of the annulation product lead to a facile total synthesis of (+)-debromoflustramine B.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Review Chemistry, Organic

Recent advances in organocatalytic asymmetric multicomponent cascade reactions for enantioselective synthesis of spirooxindoles

Yongchao Wang et al.

Summary: This review summarizes recent advances in the enantioselective construction of spirooxindoles using chiral phosphoric acids, amines, and bifunctional thiourea/squaramides as catalysts.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

Auto-tandem palladium/phosphine cooperative catalysis: synthesis of bicyclo[3.1.0]hexenes by selective activation of Morita-Baylis-Hillman carbonates

Yue Wang et al.

Summary: This study presents a new palladium/phosphine cooperative catalytic system for the synthesis of bicyclo[3.1.0]hexene derivatives, highlighting the crucial roles of both Pd and phosphine in the selective intermolecular activation of Morita-Baylis-Hillman carbonates. This strategy opens up a new avenue for efficient and economical metal/Lewis base dual catalytic systems and provides valuable clues on solving the limitations of selective activation.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

An easy and practical approach to access multifunctional cylcopentadiene- and cyclopentene-spirooxindoles via [3+2] annulation

Prakash K. Warghude et al.

Summary: A highly regioselective [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatin with aurone/thioaurone has been developed for constructing spiroheterocycles. By exploring the reactivity of Lewis bases, spirooxindole cyclopentadiene and spirooxindole fused hydroxy cyclopentene derivatives were synthesized in one pot. Experimental and DFT calculations provided insight into the reaction mechanism.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Organic

Stereoselective synthesis and applications of spirocyclic oxindoles

Alexander J. Boddy et al.

Summary: This review focuses on the development of new stereoselective approaches to spirocyclic oxindoles with spiro-3- to 8-membered rings, highlighting their importance in medicinal chemistry and as model compounds for enantioselective catalytic methodologies.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Multidisciplinary

Transformations of Modified Morita-Baylis-Hillman Adducts from Isatins Catalyzed by Lewis Bases

Zhi-Chao Chen et al.

CHEMICAL RECORD (2020)

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Lewis Base Catalysis Promoted Nucleophilic Substitutions - Recent Advances and Future Directions

Peter H. Huy

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Applied

Bifunctional Phosphonium Salt-catalyzed Enantioselective [4+2] Annulation of Isoindigos with Allenes: Access to Complex Heterocycles with Centerpiece of 4H-Pyrans

Juan Du et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Review Chemistry, Organic

Organocatalytic Synthesis of Chiral Spirooxindoles with Quaternary Stereogenic Centers

Estibaliz Sansinenea et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Tertiary Amine Lewis Base Catalysis in Combination with Transition Metal Catalysis

Gary J. Knox et al.

TOPICS IN CURRENT CHEMISTRY (2020)

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Article Chemistry, Organic

Asymmetric (4+3) and (4+1) Annulations of Isatin-derived Morita-Baylis-Hillman Carbonates to Construct Diverse Chiral Heterocyclic Frameworks

Ru-Jie Yan et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Applied

Recent Advances in Organocatalyst-Mediated Benzannulation Reactions

Lulu Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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N-Heterocyclic Carbene-Based Catalysis Enabling Cross-Coupling Reactions

Hirohisa Ohmiya

ACS CATALYSIS (2020)

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Article Chemistry, Organic

Chiral Naphthyl-C2-Indole as Scaffold for Phosphine Organocatalysis: Application in Asymmetric Formal [4+2] Cycloaddition Reactions

Tingting He et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Multidisciplinary

Recent advances in phosphine catalysis involving γ-substituted allenoates

Er-Qing Li et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Multidisciplinary

Auto-Tandem Cooperative Catalysis Using Phosphine/Palladium: Reaction of Morita-Baylis-Hillman Carbonates and Allylic Alcohols

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Synthesis of chiral spiro-cyclopentene/cyclopentadiene-oxindoles through an asymmetric [3+2] cycloaddition of isatin-derived MBH carbonates and β,γ-unsaturated α-keto esters

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TETRAHEDRON (2019)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene/Copper Cooperative Catalysis for the Asymmetric Synthesis of Spirooxindoles

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Applied

Safe, Metal-Free, and Direct Synthesis of Dialkyl Acylmethylidenehydrazine-1,1-dicarboxylates from Dimethylsulfoxonium Acylmethylides and Dialkyl Azodicarboxylates

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ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Cooperative Tertiary Amine/Chiral Iridium Complex Catalyzed Asymmetric [4+3] and [3+3] Annulation Reactions

Zhi-Chao Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Phosphine/Palladium Cooperative Catalysis: (4+3) Annulations of Morita-Baylis-Hillman Carbonates and Vinyl Benzoxazinanones

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JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Catalyst-Free Synthesis of Aminals from Indole-Derived ,-Dicyanoolefins

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SYNLETT (2019)

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Article Chemistry, Applied

N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Pentacyclic Spirooxindoles via [3+3] Annulations of Isatin-Derived Enals and Cyclic N-Sulfonyl Ketimines

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ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

pi-Conjugation expanded isoindigo derivatives and the donor-acceptor conjugated polymers: synthesis and characterization

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CHEMICAL COMMUNICATIONS (2018)

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Review Biochemistry & Molecular Biology

The Development of Biologically Important Spirooxindoles as New Antimicrobial Agents

Yan-Tao Yang et al.

CURRENT MEDICINAL CHEMISTRY (2018)

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Article Chemistry, Organic

Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita-Baylis-Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO

Sanjeeva K. Arupula et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Effective and diastereoselective preparation of dispiro[cyclopent-3'-ene]bisoxindoles via novel [3+2] annulation of isoindigos and MBH carbonates

Hong-Xia Ren et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

Lewis-Base-Catalyzed Domino Reaction of Morita-Baylis-Hillman Carbonates of Isatins with Enolizable Cyclic Carbonyl Compounds: Stereoselective Access to Spirooxindole-Pyrans

Anubha Yadav et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Review Chemistry, Multidisciplinary

Phosphine Organocatalysis

Hongchao Guo et al.

CHEMICAL REVIEWS (2018)

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Article Chemistry, Medicinal

Inhibition of p53-Murine Double Minute 2 (MDM2) Interactions with 3,3 '-Spirocyclopentene Oxindole Derivatives

Maxime Gicquel et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

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Article Chemistry, Organic

Cycloaddition of isatin-derived MBH carbonates and 3-methyleneoxindoles to construct diastereoselective cyclopentenyl bis-spirooxindoles and cyclopropyl spirooxindoles: Catalyst controlled [3+2] and [2+1] annulations

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TETRAHEDRON LETTERS (2018)

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Article Chemistry, Multidisciplinary

Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Organic

Synthesis of 6-Substituted 6H-Indolo[2,3-b]quinolines from Isoindigos

Ling Fan et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Multidisciplinary

Synthesis of Spirooxindoles Bearing Iminothiolactone Moiety from Morita-Baylis-Hillman Carbonates of Isatins and Phenyl Isothiocyanate

Beom Kyu Min et al.

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Physical

N-Heterocyclic Carbene Catalysis via the α,β-Unsaturated Acyl Azolium

Changhe Zhang et al.

ACS CATALYSIS (2017)

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Article Chemistry, Applied

Palladium-catalyzed Oxa-[4+2] Annulation of para-Quinone Methides

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ADVANCED SYNTHESIS & CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Access to dihydropyridinones and spirooxindoles: application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates

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CHEMICAL COMMUNICATIONS (2017)

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Article Chemistry, Multidisciplinary

Construction of polycyclic spirooxindoles through [3+2] annulations of Morita-Baylis-Hillman carbonates and 3-nitro-7-azaindoles

Kai-Kai Wang et al.

CHINESE CHEMICAL LETTERS (2017)

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Article Chemistry, Multidisciplinary

Engaging Allene-Derived Zwitterions in an Unprecedented Mode of Asymmetric [3+2]-Annulation Reaction

Muthukumar G. Sankar et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates

Xiaoyu Han et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

Catalyst-Controlled Switch in Chemo- and Diastereoselectivities: Annulations of Morita-Baylis-Hillman Carbonates from Isatins

Gu Zhan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Organic

Enantioselective Synthesis of Spiro[indoline-3,2′-pyrroles] through N-Heterocyclic-Carbene-Catalyzed Formal [3+2] Annulation

Chengyuan Wang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Organic

Morita-Baylis-Hillman Reaction of α,β-Unsaturated Ketones with Allylic Acetates by the Combination of Transition-Metal Catalysis and Organomediation

Ya-Qiong Li et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Organic

1-Hydroxybenzotriazole-Assisted, N-Heterocyclic Carbene Catalyzed β-Functionalization of Saturated Carboxylic Esters: Access to Spirooxindole Lactones

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JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Organic

DABCO-catalyzed unusual [4+2] cycloaddition reaction: non-substituted allenoate acts as a four-carbon synthon and facile synthesis of spirooxindoles

Yufen Liu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

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Article Chemistry, Organic

Microwave-assisted organocatalysis: phosphine-mediated Tomita Zipper cyclization affording functionalized spirooxindole

Xiao-Yan Zhang et al.

TETRAHEDRON LETTERS (2016)

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Article Chemistry, Organic

α-Regioselective [3+2] annulations with Morita-Baylis-Hillman carbonates of isatins and 2-nitro-1,3-enynes

Guang-Yao Ran et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

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Article Chemistry, Multidisciplinary

Formal [3+3] annulation of isatin-derived 2-bromoenals with 1,3-dicarbonyl compounds enabled by Lewis acid/N-heterocyclic carbene cooperative catalysis

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RSC ADVANCES (2016)

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Article Chemistry, Multidisciplinary

L-Isoleucine derived bifunctional phosphine catalyses asymmetric [3+2]-annulation of allenyl-esters and -ketones with ketimines

Muthukumar G. Sankar et al.

RSC ADVANCES (2016)

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Review Chemistry, Multidisciplinary

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

Darrin M. Flanigan et al.

CHEMICAL REVIEWS (2015)

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Article Chemistry, Multidisciplinary

An NHC-Catalyzed In Situ Activation Strategy to β-Functionalize Saturated Carboxylic Acid: An Enantioselective Formal [3+2] Annulation for Spirocyclic Oxindolo-γ-butyrolactones

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CHEMISTRY-A EUROPEAN JOURNAL (2015)

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Article Chemistry, Multidisciplinary

C2-symmetric BINOL-squaramide as efficient organocatalyst for the enantioselective α-amination of 1,3-dicarbonyl compounds with dialkyl azodicarboxylates

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CHINESE CHEMICAL LETTERS (2015)

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Review Chemistry, Medicinal

Spirooxindoles: Promising scaffolds for anticancer agents

Bin Yu et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2015)

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Article Chemistry, Organic

Diastereoselective synthesis of cyclopentanonef-used spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes

Atanu Patra et al.

ORGANIC CHEMISTRY FRONTIERS (2015)

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Article Chemistry, Applied

Phosphine-Catalyzed Asymmetric Formal [4+2] Tandem Cyclization of Activated Dienes with Isatylidenemalononitriles: Enantioselective Synthesis of Multistereogenic Spirocyclic Oxindoles

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ADVANCED SYNTHESIS & CATALYSIS (2014)

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Article Chemistry, Multidisciplinary

Conjugate Umpolung of β,β-Disubstituted Enals by Dual Catalysis with an N-Heterocyclic Carbene and a Bronsted Acid: Facile Construction of Contiguous Quaternary Stereocenters

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Multidisciplinary

Phosphine-catalyzed asymmetric [4+1] annulation of activated α,β-unsaturated ketones with Morita-Baylis-Hillman carbonates: enantioselective synthesis of spirooxindoles containing two adjacent quaternary stereocenters

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CHEMICAL COMMUNICATIONS (2014)

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Review Multidisciplinary Sciences

An overview of N-heterocyclic carbenes

Matthew N. Hopkinson et al.

NATURE (2014)

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Article Chemistry, Organic

Cooperative N-heterocyclic carbene (NHC)-Lewis acid-mediated regioselective umpolung formal [3+2] annulations of alkynyl aldehydes with isatins

Yu Zhang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

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Article Chemistry, Organic

Chiral Spirooxindole-Butenolide Synthesis through Asymmetric N-Heterocyclic Carbene-Catalyzed Formal (3+2) Annulation of 3-Bromoenals and Isatins

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ORGANIC LETTERS (2014)

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Article Chemistry, Applied

Phosphine-Catalyzed Asymmetric [4+2] Annulation of Vinyl Ketones with Oxindole-Derived α,β-Unsaturated Imines: Enantioselective Syntheses of 2′,3′-Dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones

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ADVANCED SYNTHESIS & CATALYSIS (2013)

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Article Chemistry, Multidisciplinary

Phosphine-Catalyzed Rauhut-Currier Domino Reaction: A Facile Strategy for the Construction of Carbocyclic Spirooxindoles Skeletons

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Article Chemistry, Organic

Enantioselective Synthesis of Spirooxindoles: Asymmetric [3+2] Cycloaddition of (3-Isothiocyanato)oxindoles with Azodicarboxylates

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

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Article Chemistry, Medicinal

A Potent Small-Molecule Inhibitor of the MDM2-p53 Interaction (MI-888) Achieved Complete and Durable Tumor Regression in Mice

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Article Chemistry, Organic

Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications

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Article Chemistry, Organic

Synthesis of 3,3′-Spirocyclic Oxindoles via Phosphine Catalyzed [4+2] Cyclizations

Maxime Gicquel et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Organic

Phosphine-Catalyzed [4+2] Annulation of γ-Substituent Allenoates: Facile Access to Functionalized Spirocyclic Skeletons

Erqing Li et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Multidisciplinary

An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones

Julien Dugal-Tessier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Review Chemistry, Multidisciplinary

Organocatalytic umpolung: N-heterocyclic carbenes and beyond

Xavier Bugaut et al.

CHEMICAL SOCIETY REVIEWS (2012)

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Article Chemistry, Organic

Phosphine-catalyzed domino reaction: an efficient method for the synthesis of highly functionalized spirooxazolines

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ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

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Article Chemistry, Organic

N-Heterocyclic Carbene-Catalyzed Three-Component Domino Reaction of Alkynyl Aldehydes with Oxindoles

Ding Du et al.

ORGANIC LETTERS (2012)

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Article Chemistry, Organic

Highly Enantioselective Addition of Enals to Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes: Synthesis of Spirocyclic γ-Lactams

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ORGANIC LETTERS (2012)

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Article Chemistry, Applied

Organocatalytic Asymmetric a-Amination of Unprotected 3-Aryl and 3-Aliphatic Substituted Oxindoles using Di-tert-butyl Azodicarboxylate

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ADVANCED SYNTHESIS & CATALYSIS (2011)

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Article Chemistry, Multidisciplinary

Highly diastereo- and enantioselective NHC-catalyzed [3+2] annulation of enals and isatins

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CHEMICAL COMMUNICATIONS (2011)

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Article Chemistry, Multidisciplinary

Phosphine-catalyzed highly diastereoselective [3+2] cyclization of isatin derived electron-deficient alkenes with alpha-allenic esters

Xiu-Chun Zhang et al.

CHEMICAL COMMUNICATIONS (2011)

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Article Chemistry, Organic

Tertiary Amine-Catalyzed Chemoselective and Asymmetric [3+2] Annulation of Morita-Baylis-Hillman Carbonates of Isatins with Propargyl Sulfones

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ORGANIC LETTERS (2011)

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Article Chemistry, Multidisciplinary

Robust Generation of Lead Compounds for Protein-Protein Interactions by Computational and MCR Chemistry: p53/Hdm2 Antagonists

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

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Article Chemistry, Multidisciplinary

Catalytic Asymmetric Synthesis of 3-Aminooxindoles: Enantiofacial Selectivity Switch in Bimetallic vs Monometallic Schiff Base Catalysis

Shinsuke Mouri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products

Andrey P. Antonchick et al.

NATURE CHEMISTRY (2010)

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Article Multidisciplinary Sciences

Spiroindolones, a Potent Compound Class for the Treatment of Malaria

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SCIENCE (2010)

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Review Chemistry, Multidisciplinary

Enantioselective catalysis and complexity generation from allenoates

Bryan J. Cowen et al.

CHEMICAL SOCIETY REVIEWS (2009)

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Review Chemistry, Multidisciplinary

Lewis base catalysis in organic synthesis

Scott E. Denmark et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Review Chemistry, Multidisciplinary

Phosphine-triggered synthesis of functionalized cyclic compounds

Long-Wu Ye et al.

CHEMICAL SOCIETY REVIEWS (2008)

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Article Chemistry, Medicinal

Discovery of a new class of potent, selective, and orally bioavailable CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases

Stefano Crosignani et al.

JOURNAL OF MEDICINAL CHEMISTRY (2008)

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Article Chemistry, Organic

Concise Stereocontrolled Formal Synthesis of (±)-Quinine and Total Synthesis of (±)-7-Hydroxyquinine via Merged Morita-Baylis-Hillman-Tsuji-Trost Cyclization

Peter Webber et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

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Review Chemistry, Multidisciplinary

Organocatalysis by N-heterocyclic, carbenes

Dieter Enders et al.

CHEMICAL REVIEWS (2007)

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Review Chemistry, Multidisciplinary

N-heterocyclic carbenes as organocatalysts

Nicolas Marion et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

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Review Chemistry, Multidisciplinary

Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents

Chris V. Galliford et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

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Article Chemistry, Organic

N-heterocyclic carbene catalyzed reaction of enals and 1,2-dicarbonyl compounds:: Stereoselective synthesis of spiro γ-butyrolactones

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ORGANIC LETTERS (2006)

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Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: Merging organic and transition metal catalysis

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

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Review Chemistry, Multidisciplinary

Cyclopropenylium cations, cyclopropenones, and heteroanalogues - Recent advances

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CHEMICAL REVIEWS (2003)

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Review Chemistry, Multidisciplinary

Paraherquamides, brevianamides, and asperparalines: Laboratory synthesis and biosynthesis. An interim report

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ACCOUNTS OF CHEMICAL RESEARCH (2003)

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Article Chemistry, Multidisciplinary

A catalytic carbon-phosphorus ylide reaction: Phosphane-catalyzed annulation of allylic compounds with electron-deficient alkenes

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

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Article Pharmacology & Pharmacy

Pteropodine and isopteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte

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Review Chemistry, Multidisciplinary

Reactions of electron-deficient alkynes and allenes under phosphine catalysis

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ACCOUNTS OF CHEMICAL RESEARCH (2001)

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