Recent Advances in the Asymmetric Synthesis of α-(Trifluoromethyl)-Containing α-Amino Acids

Abstract

This review article provides a comprehensive update on the development of new methods for the asymmetric synthesis of α-(trifluoromethyl)-α-amino acids, covering the literature from 2006 to mid-February 2012. Most of the methods discussed are based on asymmetric additions across the carbon–nitrogen double bond of the imines derived from esters of 3,3,3-trifluoropyruvic acid. Medium to high levels of stereocontrol can be achieved using phenylglycinol-derived chiral auxiliaries attached to the nitrogen of the corresponding imines. Among the enantioselective approaches, impressive results were achieved through the application of the Strecker­ reaction using chiral thioureas, as well as chiral Brønsted acids, as organocatalysts.

1 Introduction

2 Stoichiometric Asymmetric Syntheses of α-(Trifluoromethyl)-α-amino Acids

3 Catalytic Asymmetric Syntheses of α-(Trifluoromethyl)-α-amino Acids

4 Miscellaneous

5 Conclusions

Key words

asymmetric synthesis - fluorine - amino acids - catalysis - chiral auxiliaries

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