An efficient stereoselective synthesis of enantiomerically pure aziridine derivatives of allyl beta-D-glucopyranosides asymmetrically induced by a glucide moiety

The enantiomerically pure title aziridines were obtained by regioselective azidolysis of the 2',3'-epoxy derivatives of allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranosides, followed by cyclization of the corresponding azido alcohols by means of the PPh3 protocol. Enantiomerically pure starting epoxides were prepared by epoxidation of the corresponding allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranosides asymmetrically induced by a glucide moiety. (C) 1998 Elsevier Science Ltd. All rights reserved