Tetrahedron: Asymmetry

Kinetic resolution of α-bromophenylacetamides using quinine or Cinchona alkaloid salts

L Marzorati, JL Fejfar, CF Tormena, C Di Vitta

Index: Marzorati, Liliana; Fejfar, Jose L.; Tormena, Claudio F.; Vitta, Claudio Di Tetrahedron Asymmetry, 2012 , vol. 23, # 10 p. 748 - 753

Full Text: HTML

Citation Number: 2

Abstract

The kinetic resolution of racemic α-bromophenylacetamides 1 was achieved in the presence of benzenethiolate and Cinchona alkaloid salts as phase-transfer catalysts or benzenethiol and quinine, yielding (S)-enantioenriched α-sulfanylated products. The observed stereoselection was rationalized on the basis of the best fitting of 1 and the resolving agent in the ternary complexes.