Enantioselective synthesis of optically active homoallylamines by nucleophilic addition of chirally modified allylboranes to N-silylimines

Abstract

Enantioselectivity in the allylboration of N-silylimines with a variety of chirally modified allylboron reagents has been examined. Optically active N-sulfonylamino alcohols (16, 17 and 19) derived from D-camphor and norephedrine were found to be efficient chiral ligands for the allylboration reagent. These reagents smoothly reacted with N-silylimines to give the corresponding homoallylic amines in a high level of enantioselectivity up to 96% ee.