Copper-Catalyzed Enantioselective 1,6-Boration of para-Quinone Methides and Efficient Transformation of gem-Diarylmethine Boronates to Triarylmethanes

被引：262
作者：
Lou, Yazhou [1 ,2 ]
Cao, Peng [1 ,2 ]
Jia, Tao [1 ,2 ]
Zhang, Yongling [1 ,2 ]
Wang, Min [1 ,2 ]
Liao, Jian [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Sichuan Univ, Coll Chem Engn, Chengdu 610065, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 41期
关键词：
asymmetric catalysis; boron; copper; cross-coupling; synthetic methods; CROSS-COUPLING REACTIONS; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ASYMMETRIC BETA-BORATION; TERTIARY BORONIC ESTERS; LITHIATION/BORYLATION-PROTODEBORONATION METHODOLOGY; CONJUGATE ADDITIONS; STEREOGENIC CENTERS; CHIRAL SECONDARY; 7-CYANO-7-ETHOXYCARBONYL-1,4-BENZOQUINONE METHIDE; ANTIPROLIFERATIVE AGENTS;
D O I：
10.1002/anie.201505926
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Presented is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato) diboron to para-quinone methides. The reaction proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters. Additionally, the subsequent conversion of the derived potassium trifluoroborates into triarylmethanes with highly enantiospecificity was realized.
引用
收藏
页码：12134 / 12138
页数：5
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