Asymmetric 1,3-dipolar cycloadditions of a chiral non-racemic azomethine imine.

Chiral non racemic carbazate 1, derived from (R)-(-)-phenylglycinol, reacts regioselectively with benzaldehyde or its dimethylacetal to give an azomet hine imine. The facial, endo/exo and regio selectivities of 1,3-dipolar cyc loadditions of this reactive species with various dipolarophiles have been studied and are described in this paper. In the best cases, up to three con tiguous asymmetric centers could be generated simultaneously, in a complete enantio- and diastereoselective fashion. (C) 1999 Published by Elsevier Sc ience Ltd. All rights reserved.