Asymmetric catalytic coupling of organoboranes, alkynes, and imines with a removable (trialkylsilyloxy)ethyl group - Direct access to enantiomerically pure primary allylic amines

Abstract

The aryl substituent on the catalyst is central to the success of the title reaction (see scheme) which affords allylic amines in up to 89% ee and 91% yield with a catalyst derived from [Ni(cod)2] and a P-chiral ferrocenyl phosphane (e.g. 1). The coupling products are easily deprotected to enantiomerically enriched, tetrasubstituted primary allylic amines, which can be recrystallized to optical purity.