A Sc(OTf)3-catalyzed one-pot two-step approach for spiro-oxindole dihydropyridine derivatives initiated by N-olefination of MBH carbonates

Article Chemistry, Organic

Phosphine-Mediated Sequential [2+4]/[2+3] Annulation to Construct Pyrroloquinolines

Junhui Lin et al.

Summary: A domino [2+4]/[2+3] sequential annulation reaction of MBH carbonates with N-unprotected indoles has been developed, providing a straightforward approach for the synthesis of various pyrroloquinoline derivatives with high selectivity.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Catalytic asymmetric synthesis of 3,4′-indole-pyrazole derivatives featuring axially chiral bis-pentatomic heteroaryls

Chenghao Li et al.

Summary: In this study, axially chiral 3,4'-indole-pyrazole derivatives were successfully synthesized through the chiral phosphoric acid-catalyzed Mannich reaction. High diastereoselectivities and enantioselectivities could be obtained in most cases. The presence of a 5-pyrazolyl acetate moiety in the substrate proved crucial for improving the reactivity.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Review Chemistry, Applied

Styrene Oxide Isomerase Catalyzed Meinwald Rearrangement Reaction: Discovery and Application in Single-Step and One-Pot Cascade Reactions

Joel P. S. Choo et al.

Summary: This review summarizes the catalytic properties of styrene oxide isomerase (SOI) and discusses its applications in biocatalytic synthesis, engineering biocatalytic cascades, and metabolic engineering. The use of two-phase aqueous-organic systems in biotransformation reactions involving SOI is also highlighted.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (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

Sc(OTf)3-Mediated One-Pot Synthesis of 3,4-Disubstituted 1H-Pyrazoles and 3,5-Disubstituted Pyridines from Hydrazine or Ammonia with Epoxides

Md Shafaat Al Mehedi et al.

Summary: This article reports the synthesis of 3,4-disubstituted 1H-pyrazoles and 3,5-disubstituted pyridines by reacting epoxides with hydrazine and ammonia, respectively. Both reactions employ Sc(OTf)3 as a Lewis acid and utilize different reaction conditions for subsequent transformations.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Domino Semipinacol/Iterative Aldol/Iso-Nazarov Cyclization to Triaryl-cyclopentenone: Enantioselective Synthesis of Combretastatin A-4 Analogues

Narra Rajashekar Reddy et al.

Summary: A facile domino strategy for the synthesis of biologically active cyclopent-2-enone core containing CA-4 analogues has been developed. The methodology involves a sequence of semipinacol rearrangement, iterative aldol condensation, and iso-Nazarov cyclization reactions. Enantioselective synthesis of S-hydroxy-cyclopent-2-enones using the Sharpless AD catalyst was also achieved. Biological studies showed better inhibitory activity against cell proliferation for (S)-enantiomers than (R)-enantiomers.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Organo/Silver Dual Catalytic (3+2)/Conia-Ene Type Cyclization: Asymmetric Synthesis of Indane-Fused Spirocyclopenteneoxindoles

Dong-Ai Li et al.

Summary: This study successfully developed an efficient strategy for synthesizing spirocyclo-penteneoxindoles, which have potential biological activity. Using the thiourea/silver dual catalytic reaction of 2-(2-oxoindolin-3-yl)malononitrile with ortho-ethynyl substituted nitrostyrene in a (3 + 2)/Conia-ene type reaction, three new C-C bonds were formed within one synthetic step. The yield and selectivity of the indane-fused spirocyclopenteneoxindoles were excellent.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

[4+3]-Cycloaddition Reaction of Sulfilimines with Cyclobutenones: Access to Benzazepinones

Xiaozhou Xie et al.

Summary: The catalyst-free reaction described in this study allows for the straightforward synthesis of 1,5-dihydro-2H-benzo[b]azepin-2-ones under mild reaction conditions, with a broad substrate scope and good functional group tolerance. Additionally, a series of pyridoazepinones have been prepared using N-pyridinyl sulfilimine as the substrate.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Formal (3+1+1) Carboannulation of Morita-Baylis-Hillman Carbonates with Pyridinium Ylides: Access to Spiro-Cyclopentadiene Oxindoles

Xue Tang et al.

Summary: An efficient (3 + 1 + 1) carboannulation strategy was developed for constructing diversely functionalized Spiro-cyclopentadiene oxindoles using Morita-Baylis-Hillman carbonates and pyridinium ylides. The reaction features broad substrate scope and high chemo- and regioselectivity, with the potential to easily transform the products into interesting Spiro-cyclopenta[c] furan oxindoles.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Asymmetric Catalytic Vinylogous Addition Reactions Initiated by Meinwald Rearrangement of Vinyl Epoxides

Jinxiu Xu et al.

Summary: By utilizing chiral N,N'-dioxide/Sc-III complex catalysts, the first catalytic asymmetric multiple vinylogous addition reactions initiated by Meinwald rearrangement of vinyl epoxides were achieved, providing an efficient method for the synthesis of chiral organic compounds with high efficiency and stereoselectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Stereoselective Sc(OTf)3-Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals

Peter-Yong Wang et al.

Summary: The facile and modular access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed for their successful application in a stereoselective aldol reaction, resulting in excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is explained by a non-classical open transition state.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Metal-Free and Regioselective Synthesis of Functionalized α-Carbolines via [3+3] Annulation of Morita-Baylis-Hillman Acetates of Nitroalkenes with Iminoindolines

Sudheesh T. Sivanandan et al.

Summary: This study presents a facile, metal-free method for the synthesis of substituted alpha-carbolines from secondary Morita-Baylis-Hillman acetates of nitroalkenes. The regioselective cascade reaction of MBH acetates with tosyliminoindolines leads to the formation of various alpha-carbolines with a wide substrate scope. The reaction occurs under mild conditions and yields products in high amounts within a short reaction time, showing scalability and potential synthetic applications.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Scandium(III)-Triflate-Catalyzed Multicomponent Reactions for the Synthesis of Nitrogen Heterocycles

Luiz S. Longo et al.

Summary: This review summarizes the recent progress on the use of scandium(III) triflate as a Lewis acid catalyst for multicomponent reactions in the synthesis of nitrogen-containing heterocycles, which are valuable privileged scaffolds in Organic and Medicinal Chemistry.

CHEMISTRYSELECT (2021)

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Article Chemistry, Multidisciplinary

Catalytic asymmetric [3+2] cycloaddition of isomunchnones with methyleneindolinones

Kaixuan Wang et al.

Summary: An efficient enantioselective [3+2] cycloaddition was achieved using a chiral N,N'-dioxide/Zn(ii) complex as a Lewis acid, resulting in the synthesis of a series of chiral oxa-bridged 3-spiropiperidines with high yields, excellent dr, and excellent ee values.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Catalytic asymmetric synthesis of spirocyclobutyl oxindoles and beyond via [2+2] cycloaddition and sequential transformations

Xia Zhong et al.

Summary: The efficient asymmetric synthesis of a collection of small molecules with structural diversity is highly important to drug discovery. In this study, three distinct types of chiral cyclic compounds were accessible by enantioselective catalysis and sequential transformations. Experimental studies and DFT calculations were performed to probe the reaction mechanism, showing high selectivity and efficiency in the reaction of N-allenamides.

CHEMICAL SCIENCE (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

Catalyst-free synthesis of oxazol-2(3H)-ones from sulfilimines and diazo compounds through a tandem rearrangement/aziridination/ring-expansion reaction

Lina Song et al.

Summary: This novel synthetic method allows for the synthesis of oxazol-2(3H)-ones from common compounds without the need for high temperatures, metal catalysts, or complex substrates. The reaction is efficient and the products obtained can be easily converted into other valuable heterocyclic frameworks.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Review Chemistry, Organic

The transition-metal-catalyzed stereoselective ring-expansion of vinylaziridines and vinyloxiranes

Tanumay Sarkar et al.

Summary: In recent years, the transition-metal-aided stereoselective construction of sp(3)-carbon-rich heterocyclic scaffolds using strained-ring systems has received considerable attention. Catalytic ring-enlargement of vinylaziridines and vinyloxiranes plays a predominant role in synthesizing high sp(3)-content biorelevant heterocyclic compounds.

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, Organic

Sc(OTf)3-catalyzed [3+2]-cycloaddition of nitrones with ynones

Chun-Ting He et al.

Summary: An efficient method has been developed to access functionalized (2,3-dihydroisoxazol-4-yl) ketones by reacting nitrones with ynones or terminal ynones in a one-pot fashion, resulting in moderate to good yields.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Asymmetric organocatalysis: an enabling technology for medicinal chemistry

Bo Han et al.

Summary: Asymmetric organocatalysis has made significant contributions to organic synthesis since the early 2000s, especially in medicinal chemistry. This review provides a comprehensive overview of the specific applications of asymmetric organocatalysis in pharmaceutical synthesis, with a focus on the synthesis strategies of various bioactive molecules and their future prospects.

CHEMICAL SOCIETY REVIEWS (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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Article Chemistry, Multidisciplinary

α-Imino Gold Carbene Intermediates from Readily Accessible Sulfilimines: Intermolecular Access to Structural Diversity

Xianhai Tian et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Article Pharmacology & Pharmacy

Rational drug design, synthesis, and biological evaluation of novel chiral tetrahydronaphthalene-fused spirooxindole as MDM2-CDK4 dual inhibitor against glioblastoma

Biao Wang et al.

ACTA PHARMACEUTICA SINICA B (2020)

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Article Chemistry, Organic

Sc(OTf)3-Mediated One-Pot Synthesis of 2,3-Disubstituted Quinolines from Anilines and Epoxides

Md Shafaat Al Mehedi et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Cascade Claisen and Meinwald Rearrangement for One-Pot Divergent Synthesis of Benzofurans and 2H-Chromenes

Liyan Song et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Multidisciplinary

Catalytic asymmetric synthesis of 3,2′-pyrrolinyl spirooxindoles via conjugate addition/Schmidt-type rearrangement of vinyl azides and (E)-alkenyloxindoles

Ziwei Zhong et al.

CHEMICAL SCIENCE (2020)

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Article Chemistry, Organic

BF3•OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Chuangchuang Xu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Microwave-assisted organic acid-base-co-catalyzed tandem Meinwald rearrangement and annulation of styrylepoxides

Yi Shi et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Organic

Nucleophilic Organic Base DABCO-Mediated Chemospecific Meinwald Rearrangement of Terminal Epoxides into Methyl Ketones

Siqi Li et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

N-Pyridinyl Sulfilimines as a Source for α-Imino Gold Carbenes: Access to 2-Amino-Substituted N-Fused Imidazoles

Xianhai Tian et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Organic

Synthesis of 2-Aminoindoles through Gold-Catalyzed C-H Annulations of Sulfilimines with N-Arylynamides

Xianhai Tian et al.

ORGANIC LETTERS (2019)

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Review Chemistry, Applied

Isomerization of Epoxides

Jawahar L. Jat et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Organic

Stereoselective Assembly of Multifunctional Spirocyclohexene Pyrazolones That Induce Autophagy-Dependent Apoptosis in Colorectal Cancer Cells

Xiang Li et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Catalytic Enantioselective-House Meinwald Rearrangement: Efficient Construction of All-Carbon Quaternary Stereocenters

Dengke Ma et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Synthesis of Chiral Tetrasubstituted Azetidines from Donor-Acceptor Azetines via Asymmetric Copper(I)-Catalyzed Imido-Ylide [3+1]-Cycloaddition with Metallo-Enolcarbenes

Kostiantyn O. Marichev et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Sulfilimines as Versatile Nitrene Transfer Reagents: Facile Access to Diverse Aza-Heterocycles

Xianhai Tian et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Concise Total Synthesis of Herqulines B and C

Chi He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Review Chemistry, Multidisciplinary

Catalytic asymmetric synthesis of spirooxindoles: recent developments

Guang-Jian Mei et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Multidisciplinary

Asymmetric synthesis of tetrahydroisoquinoline-fused spirooxindoles as Ras- GTP inhibitors that inhibit colon adenocarcinoma cell proliferation and invasion

Qian Zhao et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Multidisciplinary

Chemo- and Stereoselective Cross Rauhut-Currier-Type Reaction of Tri-substituted Alkenes Containing Trifluoromethyl Groups

Xiang-Hong He et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Article Chemistry, Organic

Palladium-Catalyzed Reaction of MBH Acetates and Terminal Alkynes: Cascade Synthesis of Phenanthridine and 6-Arylethynylphenanthridine

Tanu Gupta et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Applied

Asymmetric Phosphine-Catalyzed [4+1] Annulations of o-Quinone Methides with MBH Carbonates

Tao Zhou et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Chemistry, Organic

Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

Jiru Jia et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Organic

Organocatalytic Asymmetric Synthesis of Spiro-oxindole Piperidine Derivatives That Reduce Cancer Cell Proliferation by Inhibiting MDM2-p53 Interaction

Ming-Cheng Yang et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Multidisciplinary

Synthesis of 3-(β, δ-Disubstituted) allylidene-2-oxindoles by SN2′ Reaction of Phosphorous Ylides with Carbonates of Isatin-derived Moritas-Baylis-Hillman Adducts

Su Yeon Kim et al.

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2017)

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Review Chemistry, Multidisciplinary

Inverse-Electron-Demand Diels-Alder Reactions: Principles and Applications

Zhuang Mao Png et al.

CHEMISTRY-AN ASIAN JOURNAL (2017)

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Review Chemistry, Multidisciplinary

Metal-Catalyzed Directed Regio- and Enantioselective Ring-Opening of Epoxides

Chuan Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

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Article Chemistry, Organic

Synthesis of Spirocyclic Oxindole Dihydrothiophenes by DBU-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Isothiocyanates

Yuan-Yuan Zhao et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Multidisciplinary

The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling

Ryutaro Hayashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Chemistry, Organic

The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination

Martine R. Tiddens et al.

ORGANIC LETTERS (2016)

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Article Chemistry, Organic

Efficient construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides

Sheng Wang et al.

TETRAHEDRON (2016)

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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, Multidisciplinary

Direct Thioamination of Arynes via Reaction with Sulfilimines and Migratory N-Arylation

Suguru Yoshida et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Organic

Meinwald-type rearrangement of monosubstituted epoxides to methyl ketones using an [Al porphyrin](+)[Co(CO)(4)](-) catalyst

Jessica R. Lamb et al.

Organic Chemistry Frontiers (2015)

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Review Chemistry, Multidisciplinary

The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

Chung-Yang (Dennis) Huang et al.

CHEMICAL REVIEWS (2014)

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Review Chemistry, Multidisciplinary

Vinyl Epoxides in Organic Synthesis

Jiayun He et al.

CHEMICAL REVIEWS (2014)

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Article Chemistry, Organic

Catalyst-Free Synthesis of Skipped Dienes from Phosphorus Ylides, Allylic Carbonates, and Aldehydes via a One-Pot SN2′ Allylation-Wittig Strategy

Silong Xu et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

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Article Chemistry, Multidisciplinary

Metal-Free Metathesis Reaction of C-Chiral Allylic Sulfilimines with Aryl Isocyanates: Construction of Chiral Nonracemic Allylic Isocyanates

Rebecca L. Grange et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Review Chemistry, Multidisciplinary

Isatins As Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks

Girija S. Singh et al.

CHEMICAL REVIEWS (2012)

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Review Chemistry, Multidisciplinary

Enantioselective methodologies for the synthesis of spiro compounds

Ramon Rios

CHEMICAL SOCIETY REVIEWS (2012)

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Article Chemistry, Organic

Phosphine-Catalyzed Cascade [3+2] Cyclization-Allylic Alkylation, [2+2+1] Annulation, and [3+2] Cyclization Reactions between Allylic Carbonates and Enones

Rong Zhou et al.

ORGANIC LETTERS (2011)

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Article Multidisciplinary Sciences

Spiroindolones, a Potent Compound Class for the Treatment of Malaria

Matthias Rottmann et al.

SCIENCE (2010)

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A Sc(OTf)3-catalyzed one-pot two-step approach for spiro-oxindole dihydropyridine derivatives initiated by N-olefination of MBH carbonates

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