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Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives
Journal article   Peer reviewed

Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives

Bin Hu and Li Deng
Angewandte Chemie (International ed.), Vol.57(8), pp.2233-2237
02/19/2018
PMID: 29232488

Abstract

Stereoisomerism Molecular Conformation Amino Acids - chemistry Lactams - chemical synthesis Crystallography, X-Ray Amino Acids - chemical synthesis Carboxylic Acids - chemistry Cinchona Alkaloids - chemical synthesis Imines - chemistry Pyrroles - chemistry Catalysis Cinchona Alkaloids - chemistry Lactams - chemistry
Novel cinchona alkaloid derived chiral phase-transfer catalysts enabled the highly chemo-, regio-, diastereo-, and enantioselective umpolung addition of trifluoromethyl imines to α,β-unsaturated N-acyl pyrroles. With a catalyst loading ranging from 0.2 to 5.0 mol %, this new catalytic asymmetric transformation provides facile and high-yielding access to highly enantiomerically enriched chiral trifluoromethylated γ-amino acids and γ-lactams.

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