Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations

Eduardo Sánchez-Larios; Karen Thai; François Bilodeau; Michel Gravel

doi:10.1021/ol202040b

Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations

Organic Letters ◽

10.1021/ol202040b ◽

2011 ◽

Vol 13 (18) ◽

pp. 4942-4945 ◽

Cited By ~ 56

Author(s):

Eduardo Sánchez-Larios ◽

Karen Thai ◽

François Bilodeau ◽

Michel Gravel

Keyword(s):

Stetter Reactions

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Preparation of Axially ChiralN,N′-Diarylimidazolium andN-Arylthiazolium Salts and Evaluation of Their Catalytic Potential in the Benzoin and in the Intramolecular Stetter Reactions

European Journal of Organic Chemistry ◽

10.1002/ejoc.200300762 ◽

2004 ◽

Vol 2004 (9) ◽

pp. 2025-2035 ◽

Cited By ~ 93

Author(s):

Jens Pesch ◽

Klaus Harms ◽

Thorsten Bach

Keyword(s):

Catalytic Potential ◽

Stetter Reactions

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Kinetic Resolution, Dynamic Kinetic Resolution and Asymmetric Desymmetrization by N-Heterocyclic Carbene Catalysis

Synthesis ◽

10.1055/s-0037-1612305 ◽

2019 ◽

Vol 51 (09) ◽

pp. 1871-1891 ◽

Cited By ~ 7

Author(s):

Carmela De Risi ◽

Olga Bortolini ◽

Graziano Di Carmine ◽

Daniele Ragno ◽

Alessandro Massi

Keyword(s):

Kinetic Resolution ◽

Stereoselective Synthesis ◽

Short Review ◽

Heterocyclic Carbenes ◽

Dynamic Kinetic Resolution ◽

Asymmetric Transformations ◽

Significant Interest ◽

Stetter Reactions

N-Heterocyclic carbenes (NHCs) are now well-established organocatalysts for a large number of asymmetric and non-asymmetric transformations. In the last 15 years, there has been significant interest in using NHCs in kinetic resolution (KR), dynamic kinetic resolution (DKR) and asymmetric desymmetrization reactions for the stereoselective synthesis of enantioenriched compounds, with diverse substrates and activation modes being adopted to this end. This short review brings into focus the progress made on NHC-catalyzed KR, DKR, and asymmetric desymmetrization from 2004 until December 2018. The literature discussed in this article is classified on the basis of the type of reaction involving the NHC catalyst.1 Introduction2 Acylation Strategies2.1 O-Acylation2.2 N-Acylation2.3 C-Acylation3 Aldol-Acylation Processes4 Benzoin Reactions5 Stetter Reactions6 Miscellaneous Approaches7 Conclusion

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