Asymmetric tosylation of racemic 2-hydroxyalkanamides with chiral copper catalyst

Kinetic resolution of 2-hydroxyalkanamides was performed by tosylation in the presence of copper(11) triflate and (R,R)-Ph-BOX as a catalyst. This method was successfully applied to a variety of 2-hydroxyalkanamides in high enantioselectivity with up to 92% ee, and then tosylated product was easily transformed into optically active a-amino acid derivatives. (C) 2007 Elsevier Ltd. All rights reserved.