☆ 4.6 Review

Regiodivergent Organocatalytic Reactions

CATALYSTS (2021)

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Article Chemistry, Multidisciplinary

Ligand-Controlled Copper-Catalyzed Regiodivergent Carbonylative Synthesis of α-Amino Ketones and α-Boryl Amides from Imines and Alkyl Iodides

Fu-Peng Wu et al.

Summary: Regioselective transformation is achieved in copper-catalyzed regiodivergent borocarbonylation of imines with alkyl iodides, with different ligands controlling the regioselectivity to produce either alpha-amino ketones or alpha-boryl amides selectively.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Applied

Recent Advances in Asymmetric Organomulticatalysis

Xiao Xiao et al.

Summary: This review discusses the significance and advantages of asymmetric organomulticatalysis, as well as its applications in multi-catalytic reactions. While there are challenges in this field, there are also numerous possibilities for innovation.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd-Catalyzed Regiodivergent Couplings between Indazoles and Isoprene

Wen-Shuang Jiang et al.

Summary: This study demonstrates an orthogonal regulation of nucleophilic and electrophilic sites in the regiodivergent hydroamination of isoprene with indazoles. By choosing appropriate ligands for electrophilic sites on isoprene and acid co-catalysts for nucleophilic sites on indazoles, different insertion pathways can be controlled. Preliminary experimental studies have been conducted to rationalize the mechanism and regioselectivity, providing insights into the selective functionalization of isoprene and N-functionalization of indazoles.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts

Maciej Majdecki et al.

Summary: In this study, an enantioselective phase transfer alpha-chlorination of beta-keto esters catalyzed by hybrid amide-based Cinchona derivatives was successfully reported. The reaction showed proper quantitative yields and high asymmetric induction, with use of only 0.5 mol % hybrid catalyst based on a Cinchona core allowing for highly enantioselective chlorination with various substrates.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Organocatalytic Asymmetric Cyclopropanation of 3-Acylcoumarins with 3-Halooxindoles: Access to Spirooxindole-cyclopropa[c]coumarin Compounds

Wei-Cheng Yuan et al.

Summary: The study introduces a highly diastereo- and enantioselective cyclopropanation reaction of 3-acylcoumarins with 3-halooxindoles catalyzed by an organocatalyst, resulting in compounds bearing three continuous stereocenters with high to excellent selectivities. The importance of the ammonium ylide intermediate in the catalytic process was revealed through HRMS analysis.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

C-C Bond Acylation of Oxime Ethers via NHC Catalysis

Hai-Bin Yang et al.

Summary: A novel N-heterocyclic carbene (NHC)-catalyzed strategy has been developed to efficiently activate C-C bonds without using toxic transitional metals, resulting in the synthesis of ketonitrile as a useful building block for nitrogen-containing pharmacophores.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Azetidines and their applications in asymmetric catalysis

Joseph P. Milton et al.

Summary: This article discusses the asymmetric catalytic applications of chiral azetidine-derived ligands and organocatalysts since the early 1990s, highlighting the effective synthetic opportunities they provide. It also compares and evaluates these asymmetric catalysts with aziridine- and pyrrolidine-containing analogues.

TETRAHEDRON (2021)

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Article Chemistry, Applied

Organocatalytic Enantioselective Synthesis of Tetrahydro-Furanyl Spirooxindoles via [3+2] Annulations of 3-Hydroxyoxindoles and Cyclic Ketolactams

Yue Liu et al.

Summary: Asymmetric construction of pharmacologically interesting tetrahydrofuranyl spirooxindole frameworks has been successfully achieved through organocatalytic reactions, with remarkable results in terms of yield and stereochemistry. The synthetic derivatives show significant anticancer activity against a panel of cancer cell lines, demonstrating their potential as therapeutic agents.

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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, Multidisciplinary

New Amines and Activation Modes in Asymmetric Aminocatalysis

Zhi-Chao Chen et al.

Summary: Asymmetric aminocatalysis has become a powerful strategy for the transformations of carbonyl substances over the past two decades, with research expanding the horizon of aminocatalysis through the development of cinchona-based primary amines, HOMO-raising strategy, and amine/thiol double activation catalysis. Key experiences in research include trying something different and being sensitive to differences, with a focus on honesty and understanding in supervising students, and maintaining balance between research and family through communication. Influence from PhD director Prof. Yao-Zhong Jiang is significant.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Organic

NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2H)-ones and Isoquinolines

Debabrata Barman et al.

Summary: The N-heterocyclic carbene-catalyzed tandem Stetter-aldol reactions of phthalaldehyde and alpha,beta-unsaturated ketimines yielded functionalized naphthalen-1(2H)-one derivatives as [4+2] annulation products, while the reactions of aldimines resulted in the formation of isoquinoline derivatives instead of the expected indanone derivatives as [4+1] annulation products, showcasing a novel synthetic strategy.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Chiral phosphine-catalyzed asymmetric [4+1] annulation of polar dienes with allylic derivatives: Enantioselective synthesis of substituted cyclopentenes

Hanyuan Li et al.

Summary: This study reports a chiral phosphine-catalyzed asymmetric annulation reaction, which efficiently synthesizes enantio-enriched polysubstituted cyclopentenes with high stereoselectivity.

TETRAHEDRON LETTERS (2021)

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Article Chemistry, Multidisciplinary

NHC Organocatalysis in D2O for the Highly Diastereoselective Synthesis of Deuterated Spiropyran Analogues

Pavithira Suresh et al.

Summary: Metal-free N-heterocyclic carbene (NHC) organocatalysis in D2O medium was elegantly used for the synthesis of highly diastereoselective deuterated spiropyran derivatives, achieving selective deuteration on the C5 carbon atom of the pyran ring and proving through quantum chemical calculations the preferential formation of a single diastereomer out of the possible four. The scope of NHC organocatalysis in D2O was further expanded for the synthesis of deuterated spirooxindole derivative.

CHEMISTRYSELECT (2021)

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Article Chemistry, Applied

Direct, Asymmetric Synthesis of Carbocycle-Fused Uracils via [4+2] Cycloadditions: a Noncovalent Organocatalysis Approach

Enrico Marcantonio et al.

Summary: The remote enolization strategy, strategic exploitation of noncovalent bifunctional organocatalysis, and efficient stereoselective trapping of dienolate intermediates with nitroolefins led to the successful synthesis of functionalized, chiral carbocycle-fused uracils with three contiguous stereocenters in one step, showing good levels of enantioselectivity and complete diastereocontrol. Furthermore, the enantiopure products could be obtained via simple one-cycle recrystallizations and the scaffolds could be further functionalized without losing their chiral integrity.

ADVANCED SYNTHESIS & CATALYSIS (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

Regioselective, Diastereoselective, and Enantioselective One-Pot Tandem Reaction Based on an in Situ Formed Reductant: Preparation of 2,3-Disubstituted 1,5-Benzodiazepine

Gao-feng Yang et al.

Summary: An unexpected tandem cyclization/transfer hydrogenation reaction was developed for the synthesis of chiral 2,3-disubstituted 1,5-benzodiazepines. The reaction, catalyzed by chiral phosphoric acid, exhibited moderate yields, good selectivities, and high enantiomeric ratios, providing a new method for the synthesis of this class of compounds.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Construction of the Cycl[3.2.2]azine Core via Organocatalytic [12+2] Cycloadditions

Nicolaj Inunnguaq Jessen et al.

Summary: The study developed an enantioselective [12+2] cycloaddition for constructing a chiral cycl[3.2.2]azine core, with focus on the reaction mechanism through combined experimental and computational investigations. The reaction exhibited excellent selectivity and yields, with robust adaptability to various electron-deficient 2π-components.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Mechanistically Guided Design of an Efficient and Enantioselective Aminocatalytic α-Chlorination of Aldehydes

George Hutchinson et al.

Summary: The enantioselective aminocatalytic alpha-chlorination of aldehydes has been improved by shifting to a highly selective reaction pathway involving charged intermediates using hexafluoroisopropanol as solvent. This change has resulted in matching and improving upon yields and enantioselectivities while reducing the amount of catalyst and chlorinating agents, along with more convenient reaction conditions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Catalytic Asymmetric Conjugate Addition/Hydroalkoxylation Sequence: Expeditious Access to Enantioenriched Eight-Membered Cyclic Ether Derivatives

Suo-Suo Qi et al.

Summary: A new method has been developed for the selective construction of enantioenriched eight-membered cyclic ethers by combining squaramide and DBU catalysis. The reaction yields a variety of eight-membered cyclic ethers with high stereoselectivity, showcasing the practicality of ynones as C4-syntons for synthesizing chiral medium-membered rings.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Catalytic chemodivergent annulations between α-diketones and alkynyl α-diketones

Xiangwen Kong et al.

Summary: This study has successfully achieved four unprecedented and chemodivergent reactions between alpha-diketones and alkynyl alpha-diketones, leading to the construction of various biologically important molecular scaffolds. The products also exhibit promising photophysical properties and application potential, demonstrating the great value of alpha-diketones in both synthetic chemistry and material science.

SCIENCE CHINA-CHEMISTRY (2021)

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Review Chemistry, Organic

Recent developments in next generation (S)-proline-derived chiral organocatalysts

Eusebio Juaristi

Summary: This report summarizes recent developments in the field of asymmetric organocatalysis, focusing on the design and evaluation of diamine analogs of privileged (S)-prolinols as organocatalysts, and the significant improvement of catalytic activity of (S)-proline by solvate ionic liquids and other types of ionic liquids.

TETRAHEDRON (2021)

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Review Chemistry, Organic

Squaramide Catalyzed Asymmetric Synthesis of Five- and Six-Membered Rings

Anup Biswas et al.

Summary: Chiral analogues of squaramides have proved to be efficient asymmetric catalysts in the synthesis of acyclic and cyclic chiral molecules. By utilizing several bifunctional squaramides as catalysts, a wide range of cyclic molecules bearing multiple functionalities and stereocenters have been successfully synthesized.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

N-Heterocyclic Carbene (NHC)-Catalyzed Intramolecular Stetter Reaction to Access Dibenzo-fused Seven-membered Heterocycles

Sanjay Yadav et al.

Summary: In this study, we have demonstrated a novel NHC-catalyzed transformation to access dibenzo-fused seven-membered heterocyclic compounds through intramolecular Stetter reaction at room temperature. Various dibenzo[b,f]oxepine and dibenzo[b,f]thiepine derivatives were obtained in high yields. The 1,4-dicarbonyl functionality of a representative derivative underwent additional heterocyclization via Paal-Knorr reaction.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β-Unsaturated Nitroolefins

Tapaswini Das et al.

Summary: The recent advancements in organocatalytic Michael addition reactions to alpha, beta-unsaturated nitroolefins have been discussed, highlighting the rapid innovations made possible by newly developed chiral organocatalysts and the essential role of nitroolefins as well-known Michael acceptors providing structurally necessary nitro-functionalized frameworks.

CHEMISTRYSELECT (2021)

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Article Chemistry, Multidisciplinary

Catalytic Asymmetric Synthesis of Benzobicyclo[3.2.1]octanes

Mohammed Anif Pasha et al.

Summary: By utilizing a quinine-thiourea-catalyzed sequential reaction, Lawsone aldehydes were transformed into chiral methanobenzo[f]azulenes/methanodibenzo[a,d][7]annulenes with high diastereomeric ratio and enantiomeric excess. This approach is valuable for the synthesis of important antibiotics due to the nature of the final molecules.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Organic

Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates

Tingting Yan et al.

Summary: A phosphine-catalyzed olefinic cross-coupling reaction between benzyl halides and fumarates has been described, providing trisubstituted alkenes with good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Catalytic asymmetric construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements

Wande Zhang et al.

Summary: An organocatalytic asymmetric process was reported for the construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements with high yield and excellent diastereoselectivity and enantioselectivity. The process features mild reaction conditions, simple operation, broad substrate scope, and good practicability as demonstrated by gram-scale reactions.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Organic

Enantioselective [3+2] annulation of 3-hydroxymaleimides with quinone monoimines

Jiayan Zhang et al.

Summary: In this study, enantioselective [3 + 2] annulation of 3-hydroxymaleimides with quinone monoimines was achieved using a chiral phosphoric acid catalyst. Various novel succinimide fused dihydrobenzofurans with two continuous quaternary stereocenters were obtained in moderate to excellent yields and enantioselectivities, with the absolute configuration of one product confirmed by X-ray crystal structural analysis.

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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Review Chemistry, Multidisciplinary

NHC-catalyzed covalent activation of heteroatoms for enantioselective reactions

Runjiang Song et al.

Summary: This review evaluates and summarizes the covalent activation of heteroatoms enabled by N-heterocyclic carbene (NHC) organic catalysts for enantioselective reactions. Sulfur, oxygen, and nitrogen atoms can be activated in this manner to construct chiral carbon-heteroatom bonds with high optical enantioselectivities. The key lies in the formation of intermediates covalently bound to the NHC catalyst, in which the heteroatom of the substrate is activated as a nucleophilic reactive site.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

N-Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N-hydroxysuccinimide ester formation

Ashmita Singh et al.

Summary: A facile method for the amidation of aldehydes by a cascade approach has been developed using NHC as the catalyst and NHS as the mediator. The method utilizes TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS to form active esters, which were easily converted into amides. The drug moclobemide was successfully synthesized using this methodology to demonstrate its practical utility.

NEW JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Enantiodivergent synthesis of tricyclic chromans: Remote nucleophilic groups switch selectivity in catalytic asymmetric cascade reactions of trifunctional substrates

Zhongwen Sun et al.

Summary: An efficient and unified approach to the enantioselective synthesis of two important classes of tricyclic chroman scaffolds via site-selective organocatalytic asymmetric cascade reactions of newly designed phenol-based trifunctional substrates is described. The enantioselectivities of this reaction can be modified by changing the remote nucleophilic groups of the substrates.

GREEN SYNTHESIS AND CATALYSIS (2021)

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Article Chemistry, Organic

NHC-catalyzed oxindole synthesis via single electron transfer

Chengming Wang et al.

Summary: This transition-metal and aldehyde free, NHC-catalyzed, redox-neutral oxindole synthesis method has a broad substrate scope and good functional group tolerance, and can be easily scaled up. The reaction possibly involves NHC-facilitated single electron transfer induced intramolecular radical cyclization, and the oxindole products can be easily converted into various useful compounds.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Multidisciplinary

Enamides and dienamides in phosphoric acid-catalysed enantioselective cycloadditions for the synthesis of chiral amines

Thomas Varlet et al.

Summary: Chiral substituted cyclic amines are important in organic synthesis, with stable and easy to synthesize enamides and dienamides serving as versatile building blocks for the preparation of chiral amines. The exceptional synergy between these synthetic synthons and chiral phosphoric acid catalysts has been successfully utilized to develop formal cycloadditions with high enantioselectivity, allowing access to chiral cyclic amines with varying ring sizes.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Organic

Facile access to benzofuran-fused tetrahydropyridines via catalytic asymmetric [4+2] cycloaddition of aurone-derived 1-azadienes with 3-vinylindoles

Wai Lean Koay et al.

Summary: A highly enantioselective [4 + 2] cycloaddition reaction has been developed for the reaction of aurone-derived 1-azadienes with 3-vinylindoles using chiral phosphoric acids as catalysts. This reaction yields a wide range of benzofuran-fused tetrahydropyridines with three contiguous stereogenic centers, in good yields and with excellent diastereo- and enantio-selectivities.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

Organocatalytic enantioselective [2+4]-annulation of γ-substituted allenoates with N-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines

Xing Guo et al.

Summary: An enantioselective [2 + 4]-annulation of gamma-substituted allenoates with N-acyldiazenes has been developed for the first time, resulting in a broad range of 1,3,4-oxadiazine derivatives in good to excellent yields with high stereoselectivities using an l-proline-derived DMAP analogue as the catalyst.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Organic

Conjugated ynones in catalytic enantioselective reactions

Linqing Wang et al.

Summary: Conjugated ynones are versatile substrates with unique reactivity, compatible with various catalytic conditions, making them important tools for asymmetric synthesis.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Organic

Organocatalytic regio-, diastereo- and enantioselective γ-additions of isoxazol-5(4H)-ones to β,γ-alkynyl-α-imino esters for the synthesis of axially chiral tetrasubstituted α-amino allenoates

Fushuai Li et al.

Summary: Chiral phosphoric acid catalyzed a regio-, diastereo- and enantioselective reaction of isoxazol-5(4H)-ones with beta,gamma-alkynyl-alpha-imino esters, allowing for high yields of diverse alpha-imino allenoates with an adjacent quaternary carbon stereocenter and an axially chiral tetrasubstituted allene motif.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

N-Heterocyclic carbene (NHC)-catalyzed intramolecular benzoin condensation-oxidation

Killari Satyam et al.

Summary: The NHC-catalyzed intramolecular benzoin condensation-oxidation allows for the expedient synthesis of diverse cyclic 1,2-diketones incorporated in dibenzo-fused seven-membered heterocycles in good to excellent yields under ambient conditions. The transformation appears to proceed through the benzoin intermediate followed by aerobic oxidation.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Organic

Advances in organocatalytic asymmetric reactions of vinylindoles: powerful access to enantioenriched indole derivatives

Man-Su Tu et al.

Summary: Chemists have successfully synthesized a variety of chiral indole derivatives with optical purity and structural complexity through the design and development of indole-containing platform molecules and their related catalytic asymmetric reactions. Vinylindoles have been proven to be an effective platform molecule for accessing enantioenriched indole derivatives via catalytic asymmetric reactions.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

Yu-Qi Gao et al.

Summary: The study presents a tandem asymmetric Michael-addition/cyclization of cyclic 1,3-dicarbonyl compounds to beta,gamma-unsaturated alpha-ketoesters catalyzed by chiral phosphoric acid, providing a facile approach for the construction of enantioenriched 9-alkyl tetrahydroxanthenones in high yields with good to high enantioselectivities, a common framework in natural products and pharmaceutical molecules.

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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Review Chemistry, Applied

Proline and its Derivatives as Organocatalysts for Multi- Component Reactions in Aqueous Media: Synergic Pathways to the Green Synthesis of Heterocycles

B. S. Vachan et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Applied

Organocatalytic Enantioselective Regiodivergent C-H Bond Functionalization of 1-Naphthols with 1-Azadienes

Chen Zhang et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels-Alder Reactions

Thomas Varlet et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Organic

Asymmetric Michael reaction promoted by chiral thiazolidine-thiourea catalyst

Tiago Lima da Silva et al.

TETRAHEDRON (2020)

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Supported Bifunctional Chiral Thioureas as Catalysts in the Synthesis of 3-Amino-2-Oxindoles through Enantioselective aza-Friedel-Crafts Reaction: Application in Continuous Flow Processes

Marta Rodriguez-Rodriguez et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Regio-Divergent C-H Alkynylation with Janus Directing Strategy via Ir(III) Catalysis

Xianwei Li et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

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Article Chemistry, Organic

Mechanism, Chemoselectivity, and Stereoselectivity of NHC-Catalyzed Asymmetric Desymmetrization of Enal-Tethered Cyclohexadienones

Yang Xiao et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Regio- and Enantioselective α,γ-Dialkylation of α,β-Unsaturated Aldehydes Through Cascade Organocatalysis

Mahesh S. Kutwal et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

DABCO-Catalyzed Michael/Alkylation Cascade Reactions Involving α-Substituted Ammonium Ylides for the Construction of Spirocyclopropyl Oxindoles: Access to the Powerful Chemical Leads against HIV-1

Lin Chen et al.

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Article Chemistry, Physical

Lewis Base-Catalyzed Amino-Acylation of Arylallenes via C-N Bond Cleavage: Reaction Development and Mechanistic Studies

Zheng-Bing Zhang et al.

ACS CATALYSIS (2020)

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Article Chemistry, Applied

Diversity-Oriented Synthesis of Spirocyclohexene Indane-1,3-diones and Coumarin-Fused Cyclopentanes via an Organobase-Controlled Cascade Reaction

Min Wang et al.

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Ligand-Regulated Regiodivergent Hydrosilylation of Isoprene under Iron Catalysis

Chang-Sheng Kuai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Cyclic 1-Azadienes in the Organocatalytic Inverse-Electron-Demand Aza-Diels-Alder Cycloadditions

Anna Skrzynska et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Enantioselective Construction of Vicinal Sulfur-functionalized Quaternary and Tertiary Stereocenters via Organocatalytic Michael Addition of 5H-Thiazol-4-ones to 1-Azadienes

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Recent Advances in Squaramide-Catalyzed Asymmetric Mannich Reactions

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The Vinylogous Michael Addition of 3-Alkylidene-2-oxindoles to β,γ-Unsaturated α-Keto Esters by Bifunctional Cinchona Alkaloids

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Improvement of primary-amine-catalyzed asymmetric α-benzoyloxylation of α-branched enals by a synergistic effect of water and sulfonic acids

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Asymmetric Dearomative Cascade Multiple Functionalizations of Activated N-Alkylpyridinium and N-Alkylquinolinium Salts

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Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts

Maciej Majdecki et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Highly Diastereo- and Enantioselective Synthesis of Isoxazolone-Spirooxindoles via Squaramide-Catalyzed Cascade Michael/Michael Addition Reactions

Yu Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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N-Heterocyclic carbene (NHC) organocatalysis using aliphatic aldehydes

Shilpa Barik et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Organic

Stereo- and Regioselective Construction of Spirooxindoles Having Continuous Spiral Rings via Asymmetric [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Thioaurone Derivatives

Hou-Ze Gui et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines

Hui Liu et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Organic

Diastereodivergent aminocatalyzed spirocyclization strategies using 4-alkylideneisoxazol-5-ones and methyl vinyl ketones

Amanda F. da Silva et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

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Review Chemistry, Multidisciplinary

Chemodivergent reactions

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A theoretical review for novel Lewis base amine/imine-catalyzed reactions

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Organocatalytic Asymmetric Formal [3+3]-Cycloaddition to Access 2,3-Diazaspiro[4.5]deca-3,6-dien-1-ones

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Formal oxo- and aza-[3+2] reactions of aenaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves

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Diazaphosphinyl radical-catalyzed deoxygenation of α-carboxy ketones: a new protocol for chemo-selective C-O bond scission via mechanism regulation

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Cooperative photoredox and chiral hydrogen-bonding catalysis

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A PPh3-catalyzed sequential annulation reaction to construct cyclopentane-fused dihydropyrazolone-pyrrolidinediones

Cheng Cheng et al.

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Construction of chiral chroman scaffolds via catalytic asymmetric (4+2) cyclizations of para-quinone methide derivatives with 3-vinylindoles

Shu-Fang Wu et al.

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H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins

Pei-Gang Ding et al.

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Organocatalytic asymmetric Friedel-Crafts alkylation/hemiketalization/lactonization cascade reactions: highly enantioselective synthesis of furo[2,3-b]benzofuranones

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Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

Jiang-Bo Wen et al.

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Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives

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Chemo-selective Synthesis of [indoline-3,4 '-isoxazolo[5,4-b]pyridine Fused spirooxindole Derivatives via Bronsted Acid Catalysed Three-Component Tandem Knoevenagel/Michael Addition Reaction

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Organocatalytic Asymmetric Cascade Reactions Based on Gamma-Nitro Carbonyl Compound

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Breaking Aromaticity with Aminocatalysis: A Convenient Strategy for Asymmetric Synthesis

Artur Przydacz et al.

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Highly regioselective α-alkylation of α,β,γ,δ-unsaturated aldehydes

Venkata M. D. Padmaja et al.

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Asymmetric Diels-Alder Reaction of 3-Vinylindoles and Nitroolefins Promoted by Multiple Hydrogen Bonds

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Synthesis of Enantioenriched 3-Amino-3-Substituted Oxindoles by Stereoselective Mannich Reaction Catalyzed by Supported Bifunctional Thioureas.

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Catalytic Regioselective γ-Methylenation of α,β-Unsaturated Aldehydes Using Formaldehyde via Vinylogous Aldol Condensation

Mahesh S. Kutwal et al.

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Profiling the Privileges of Pyrrolidine-Based Catalysts in Asymmetric Synthesis: From Polar to Light-Driven Radical Chemistry

Alberto Vega-Penaloza et al.

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Lewis Base/Bronsted Acid Co-Catalyzed Asymmetric Thiolation of Alkenes with Acid-Controlled Divergent Regioselectivity

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Divergent synthesis of spirocyclopentene-pyrazolones and pyrano[2,3-c]-pyrazoles via Lewis base controlled annulation reactions

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Asymmetric Aza-Henry Reaction of Indolenines Mediated by a Cinchona-Alkaloid-Thiourea Organocatalyst

You-Dong Shao et al.

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Enantioselective γ-Alkylation of α,β-Unsaturated Aldehydes Using New Cinchona-Based Primary Amine Catalyst

Yong-Shuang Huang et al.

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Asymmetric Formal Vinylogous Iminium Ion Activation for Vinyl-Substituted Heteroaryl and Aryl Aldehydes

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Divergent and Scalable Synthesis of α-Hydroxy/Keto-β-amino Acid Analogues by the Catalytic Enantioselective Addition of Glyoxylate Cyanohydrin to Imines

Takeshi Nanjo et al.

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Organocatalytic Asymmetric Synthesis of Cyclic Compounds Bearing a Trifluoromethylated Stereogenic Center: Recent Developments

Xiang-Hong He et al.

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Asymmetric Formal [5+3] Cycloadditions with Unmodified Morita-Baylis-Hillman Alcohols via Double Activation Catalysis

Qian-Qian Yang et al.

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Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones -The Switchable [4+2] or [4+2]/[3+2] Cycloaddition

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Diastereodivergent construction of bispiro[oxindole-bi-pyrrolidine]s with four consecutive stereocenters via asymmetric [3+2] cycloaddition of 2,3-dioxopyrrolidines using identical catalysts

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Base-promoted regiodivergent allylation of N-acylhydrazones with Morita-Baylis-Hillman carbonates by tuning the catalyst

Fang Sun et al.

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A formal [4+2] cycloaddition of sulfur-containing alkylidene heterocycles with allenic compounds

Vojtech Docekal et al.

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Lewis base catalyzed regioselective cyclization of allene ketones or -methyl allene ketones with unsaturated pyrazolones

Cheng Cheng et al.

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Metal-catalyzed regiodivergent organic reactions

Carmen Najera et al.

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Regio- and Diastereodivergent [4+2] Cycloadditions with Cyclic 2,4-Dienones

Wei Xiao et al.

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Bifunctional Thiourea-Ammonium Salt Catalysts Derived from Cinchona Alkaloids: Cooperative Phase-Transfer Catalysts in the Enantioselective Aza-Henry Reaction of Ketimines

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Asymmetric Fluorination of α-Branched Aldehydes by Chiral Primary Amine Catalysis: Reagent-Controlled Enantioselectivity Switch

Linfeng Cui et al.

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Chiral Bifunctional Thioureas and Squaramides and Their Copolymers as Recoverable Organocatalysts. Stereoselective Synthesis of 2-Substituted 4-Amino-3-nitrobenzopyrans and 3-Functionalized 3,4-Diamino-4H-Chromenes

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Remote Asymmetric Oxa-Diels Alder Reaction of 5-Allylic Furfurals via Dearomatizative Tetraenamine Catalysis

Xiao-Long He et al.

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Primary Aminothiourea-Catalyzed Enantioselective Synthesis of Rauhut-Currier Adducts of 3-Arylcyclohexenone with a Tethered Enone on the Aryl Moiety at the Ortho-Position

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Proline-Catalyzed Asymmetric -Amination in the Synthesis of Bioactive Molecules

Pradeep Kumar et al.

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Organocatalytic and Regiodivergent Mannich Reaction of Ketones with Benzoxazinones

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Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

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Phosphine Organocatalysis

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Organocatalytic Regiodivergent C-C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks

Jian Cao et al.

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Highly enantioselective Michael addition of pyrazolin-5-ones to nitroolefins catalyzed by cinchona alkaloid derived 4-methylbenzoylthioureas

Mengchen Yang et al.

CHIRALITY (2018)

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Synthesis of Enantioenriched Bromohydrins via Divergent Reactions of Racemic Intermediates from Anchimeric Oxygen Borrowing

Yi-Ming Cao et al.

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BrOnsted acid-catalysed regiodivergent phosphorylation of 2-indolylmethanols to synthesize benzylic site or C3-phosphorylated indole derivatives

Long Chen et al.

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DBU-Catalyzed Desymmetrization of Cyclohexadienones: Access to Vicinal Diamine-Containing Heterocycles

Hongxing Jin et al.

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Asymmetric Michael addition between kojic acid derivatives and unsaturated ketoesters promoted by C2-symmetric organocatalysts

Alexey A. Kostenko et al.

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Highly Regio- and Enantioselective γ-Alkylation of Linear α,β-Unsaturated Aldehydes

Mahesh S. Kutwal et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Cinchona Alkaloid Catalyzed Enantioselective [4+2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans

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Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis

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Switchable regioselectivity in amine-catalysed asymmetric cycloadditions

Zhi Zhou et al.

NATURE CHEMISTRY (2017)

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Phosphine-catalyzed [3+2] and [4+2] annulation reactions of ynones with barbiturate-derived alkenes

Xing Gao et al.

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NHC-catalyzed regiodivergent syntheses of difunctionalized 3-pyrazolidinones from α-bromoenal and monosubstituted hydrazine

Chenxia Yu et al.

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Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3+2] annulations of aurones and an allenoate

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CHEMICAL SCIENCE (2017)

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Cinchona-Based Primary Amine Catalyzed a Proximal Functionalization of Dienamines: Asymmetric α-Fluorination of α-Branched Enals

Satoru Arimitsu et al.

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NHC-catalyzed enantioselective synthesis of dihydropyran-4-carbonitriles bearing all-carbon quaternary centers

Qiuju Wu et al.

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Squaramide-Catalyzed Asymmetric Reactions

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Divergent C-H Annulation for Multifused N-Heterocycles: Regio- and Stereospecific Cyclizations of N-Alkynylindoles

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The first organocatalytic, ortho-regioselective inverse-electron-demand hetero-Diels-Alder reaction

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Transition metal-catalyzed site- and regio-divergent C-H bond functionalization

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Switchable divergent asymmetric synthesis via organocatalysis

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Asymmetric cycloaddition reactions catalysed by diarylprolinol silyl ethers

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Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

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Organocatalytic asymmetric formal arylation of benzofuran-2(3H)-ones with cooperative visible light photocatalysis

Yang Liu et al.

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Asymmetric Mannich Reaction of Aryl Methyl Ketones with Cyclic Imines Benzo[e][1,2,3]oxathiazine 2,2-Dioxides Catalyzed by Cinchona Alkaloid-based Primary Amines

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CHEMISTRY-AN ASIAN JOURNAL (2016)

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A Multifaceted Directing Group Switching Ynones as Michael Donors in Chemo-, Enantio-, and γ-Selective 1,4-Conjugate Additions with Nitroolefins

Weiwei Liu et al.

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The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Sean M. Maddox et al.

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Aminocatalytic Enantioselective Cycloadditions

Jose L. Vicario

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The Diarylprolinol Silyl Ethers: Ten Years After

Bjarke S. Donslund et al.

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Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction

Chang Guo et al.

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Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

Craig D. Campbell et al.

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A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

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Chemoselective N-Heterocyclic Carbene-Catalyzed Cascade of Enals with Nitroalkenes

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Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

Alejandro Cabanillas et al.

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Solvent-controlled nucleophilic trifluoromethylthiolation of Morita-Baylis-Hillman carbonates: dual roles of DABCO in activating the Zard's trifluoromethylthiolation reagent and the MBH carbonates

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Stereoselective synthesis of epsilon-lactones or spiro-heterocycles through NHC-catalyzed annulation: divergent reactivity by catalyst control

Min Wang et al.

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Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by Cinchona Alkaloid Derivatives

Ying Jin et al.

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Exploring the Vinylogous Reactivity of Cyclohexenylidene Malononitriles: Switchable Regioselectivity in the Organocatalytic Asymmetric Addition to Enals Giving Highly Enantioenriched Carbabicyclic Structures

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N-Heterocyclic Carbene Catalyzed Switchable Reactions of Enals with Azoalkenes: Formal [4+3] and [4+1] Annulations for the Synthesis of 1,2-Diazepines and Pyrazoles

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Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies

Eoin Gould et al.

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Diastereo- and enantioselective nitro-Mannich reaction of α-substituted nitroacetates to N-phosphoryl imines catalyzed by cinchona alkaloid thiourea organocatalysts

Weidong Fan et al.

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Recent efforts directed to the development of more sustainable asymmetric organocatalysis

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Catalytic [2+2] and [3+2] cycloaddition reactions of allenoates with cyclic ketimines

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Nitrogen- and Phosphorus-Containing Lewis Base Catalyzed [4+2] and [3+2] Annulation Reactions of Isatins with But-3-yn-2-one

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Enantioselective organocatalytic aldol reaction using small organic molecules

Vishnumaya Bisai et al.

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Phosphine- and Nitrogen-Containing Lewis Base Catalyzed Highly Regioselective and Geometric Selective Cyclization of Isatin Derived Electron-Deficient Alkenes with Ethyl 2,3-Butadienoate

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Enantioselective α- and γ-Alkylation of α,β-Unsaturated Aldehydes Using Dienamine Activation

Julian Stiller et al.

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Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations

Masahiro Terada

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Cinchona Alkaloids in Asymmetric Organocatalysis

Tommaso Marcelli et al.

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Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions

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Proline-catalysed Mannich reactions of acetaldehyde

Jung Woon Yang et al.

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The advent and development of organocatalysis

David W. C. MacMillan

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Proline and Lewis base co-catalyzed addition of α,β-unsaturated aldehydes to nitrostyrenes

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Asymmetric enamine catalysis

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Iminium catalysis

Anniina Erkkila et al.

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Asymmetric organocatalysis

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Highly enantioselective epoxidation of 2-methylnaphthoquinone (vitamin K3) mediated by new Cinchona alkaloid phase-transfer catalysts

Albrecht Berkessel et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

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Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides:: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols

Gabriela Guillena et al.

TETRAHEDRON-ASYMMETRY (2006)

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Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: Tandem aminoxylation/O-N bond heterolysis reactions

DB Ramachary et al.

ORGANIC LETTERS (2005)

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One-pot asymmetric synthesis of β-cyanohydroxymethyl α-amino acid derivatives:: Formation of three contiguous stereogenic centers

S Watanabe et al.

ORGANIC LETTERS (2002)

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Proline-catalyzed asymmetric reactions

B List

TETRAHEDRON (2002)

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Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde

A Córdova et al.

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New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction

KA Ahrendt et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)

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Proline-catalyzed direct asymmetric aldol reactions

B List et al.

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