1,6-Conjugate addition of para-quinone methides using gem-diborylcarbanions: Practical access to gem-diborylalkanes bearing vicinal tertiary/quaternary stereocenters

Abstract

A novel, efficient and pragmatic method to prepare gem-diboron products with vicinal tertiary/quaternary stereocenters using LiTMP-mediated 1,6-conjugate addition of gem-diborylalkanes to para-quinone methides was described for the first time. The results showed that various gem-diboron products with vicinal tertiary and quaternary stereocenters could be formed within 15 ​min at ambient temperature. This simple protocol has also been applied for the efficient synthesis of the analogue of Bedaquiline.