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

Article abstract of DOI:10.1016/S0040-4039(99)00610-3

Chiral non racemic carbazate 1, derived from (R)-(-)-phenylglycinol, reacts regioselectively with benzaldehyde or its dimethylacetal to give an azomethine imine. The facial, endo/exo and regio selectivities of 1,3- dipolar cycloadditions of this reactive species with various dipolarophiles have been studied and are described in this paper. In the best cases, up to three contiguous asymmetric centers could be generated simultaneously, in a complete enantio- and diastereoselective fashion.