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

被引：4

作者：

Zi, Pu-Zhang ^{[1
]}

Liu, Xing -Bang ^{[1
]}

Zhao, Quan-Hong ^{[1
]}

He, Min ^{[1
]}

Huang, Yuan ^{[1
]}

机构：

[1] Xi An Jiao Tong Univ, Sch Pharm, Dept Med Chem, Xian 710061, Peoples R China

来源：

GREEN SYNTHESIS AND CATALYSIS | 2024年 / 5卷 / 01期

基金：

中国国家自然科学基金;

关键词：

gem-Diborylalkanes; Quaternary stereocenter; Conjugate addition; para-Quinone methides; Organoboron compounds; NATURAL-PRODUCTS; CARBON; CONSTRUCTION; 1,1-DIBORYLALKANES; DIBORYLATION; CARBANIONS; ALDEHYDES; ESTERS; BORON; ACID;

D O I：

10.1016/j.gresc.2022.12.003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：68 / 72

页数：5

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