Tetrahedron Letters

Fast ester cleavage of sterically hindered α-and β-aminoesters under non-aqueous conditions. Application to the kinetic resolution of aziridine esters

V Alezra, C Bouchet, L Micouin, M Bonin, HP Husson

Index: Alezra, Valerie; Bouchet, Celine; Micouin, Laurent; Bonin, Martine; Husson, Henri-Philippe Tetrahedron Letters, 2000 , vol. 41, # 5 p. 655 - 658

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Citation Number: 14

Abstract

In the preceeding paper we reported that aziridines 1 could be deprotonated and functionalized in a stereoselective way. 1 However, the obtention of each diastereomer required a chromatographic separation which proved to be tedious on a multigram scale. We therefore decided to investigate the ester cleavage of such species under kinetic resolution, which could lead to a diastereomerically pure water-soluble aziridino acid on the one hand, and its epimeric ester on the other ...