Cycloadditions of chiral carbonyl ylides with imine dipolarophiles as a route to enantiomerically pure alpha-amino-beta-hydroxy acids

Gan, Y., Harwood, L.M. ORCID: https://orcid.org/0000-0002-8442-7380, Richards, S.C., Smith, I.E.D. and Vinader, V. (2009) Cycloadditions of chiral carbonyl ylides with imine dipolarophiles as a route to enantiomerically pure alpha-amino-beta-hydroxy acids. Tetrahedron-Asymmetry, 20 (6-8). pp. 723-725. ISSN 0957-4166 doi: 10.1016/j.tetasy.2009.02.029

Abstract/Summary

The preparation of enantiomerically pure threo-beta-amino-alpha-hydroxy acids via 1,3-dipolar cycloadditions of imine dipolarophiles with the chiral isomunchnone derived from (5R)-5-phenylmorpholin-3-one 1 is described. The cycloadducts were obtained with excellent diastereofacial- and exo-selectivity. Subsequent hydrolysis and chemoselective exocyclic amide cleavage afforded the threo-beta-amino-alpha-hydroxy acids with recovery of the initial chiral auxiliary. (C) 2009 Published by Elsevier Ltd.