Asymmetric synthesis of propargylamides via 3,3'-disubstituted binaphthol-modified alkynylboronates

Abstract

[reaction: see text] Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.