Enantioselective Arylation of 2-methylacetoacetates Catalyzed by CuI/trans-4-hydroxy-L-proline at Low Reaction Temperatures

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2006 Dec 15

PMID 17165754

Citations 30

Authors

Xiaoan Xie

Yu Chen

Dawei Ma

Affiliations

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Abstract

CuI/trans-4-hydroxy-l-proline-catalyzed coupling reaction of 2-iodotrifluoroacetanilides with 2-methylacetoacetates took place at -45 degrees C to create alpha-aryl all-carbon quaternary centers enantioselectively. Up to 93% ee was achieved when tert-butyl ester was used. The combination of ligand, ortho substituent (participation of NHCOCF3), and solvent effects was shown to account for these unprecedentedly mild reaction conditions.

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