期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 2, 页码 1069-1077出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c11750
关键词
-
资金
- Samsung Science and Technology Foundation [SSTF-BA1701-11]
- Institute for Basic Science in Korea [IBS-R10-A1]
A copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides was reported in this study. The combination of copper(I) bromide and H-8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system, providing various enantioenriched homoallylic boronate esters under mild conditions. Experimental and theoretical studies elucidated the reaction mechanism and revealed the enatiotopic-group-selective trans-metalation of gem-diborylalkanes with chiral copper complex.
We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H-8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective trans-metalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral alpha-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据