Pu-Zhang Zi, Xing-Bang Liu, Quan-Hong Zhao, Min He, Yuan Huang
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1,6-Conjugate addition of para-quinone methides using gem-diborylcarbanions: Practical access to gem-diborylalkanes bearing vicinal tertiary/quaternary stereocenters
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.
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