Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes

被引：128

作者：

Joannou, Matthew V. ^{[1
]}

Moyer, Brandon S. ^{[1
]}

Meek, Simon J. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 19期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; ORGANIC-SYNTHESIS; ROOM-TEMPERATURE; HYDROBORATION; ALKENES; ESTERS; BORON; CARBANIONS;

D O I：

10.1021/jacs.5b03477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first catalytic enantio- and diastereoselective synthesis of 1;2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., arid 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the alpha-boryl component.

引用

页码：6176 / 6179

页数：4