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 wit...

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Bibliographic Details
Published in:Green synthesis and catalysis 2024-02, Vol.5 (1), p.68-72
Main Authors: Zi, Pu-Zhang, Liu, Xing-Bang, Zhao, Quan-Hong, He, Min, Huang, Yuan
Format: Article
Language:English
Subjects:
Conjugate addition
gem-Diborylalkanes
Organoboron compounds
para-Quinone methides
Quaternary stereocenter
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Summary: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. An efficient method was developed for the synthesis of gem-diboryl alkanes with vicinal tertiary and quaternary stereocenters using unprecedented 1,6-conjugate addition of gem-diborylcarbanions to para-quinone methides. [Display omitted]
ISSN:2666-5549
2666-5549
DOI:10.1016/j.gresc.2022.12.003