Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration

被引：297

作者：

Imao, Daisuke ^{[1
]}

Glasspoole, Ben W. ^{[1
]}

Laberge, Veronique S. ^{[1
]}

Crudden, Cathleen M. ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 14期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ASYMMETRIC-SYNTHESIS; PALLADIUM-CATALYST; ORGANIC HALIDES; MILD CONDITIONS; ALKYL BROMIDES; VINYL ARENES; HYDROBORATION; ARYL; CHLORIDES; ACID;

D O I：

10.1021/ja8094075

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use of silver oxide as a base and the presence of at least 8 equiv of triphenyl phosphine per Pd are required. The reaction proceeds with >90% retention of configuration in all cases except one. Remarkably, the linear boronate ester does not react under these conditions.

引用

页码：5024 / +

页数：3

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