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

ABSTRACT: Novel cinchona alkaloid derived chiral phase-transfer catalysts enabled the highly chemo-, regio-, diastereo-, and enantioselective umpolung addition of trifluoromethyl imines to ?,?-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 ?-amino acids and ?-lactams.

SUBMITTER: Hu B

PROVIDER: S-EPMC6408948 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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

Hu Bin B Deng Li L

Angewandte Chemie (International ed. in English) 20180118 8

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. ...[more]

PMID: 29232488

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