Boronic Esters in Asymmetric Synthesis

被引：222

作者：

Matteson, Donald S. ^{[1
]}

机构：

[1] Washington State Univ, Pullman, WA 99164 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 20期

基金：

美国国家卫生研究院;

关键词：

DIRECTED CHIRAL SYNTHESIS; TRANSITION-STATE ANALOG; X-RAY-STRUCTURE; SEX-PHEROMONE; DRUGSTORE BEETLE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; INSECT PHEROMONES; AMINO-ACIDS; HOMOLOGATION;

D O I：

10.1021/jo4013942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The author's work on (alpha-haloalkyl)boronic esters as reagents for asymmetric synthesis is reviewed. Diastereomeric ratios exceeding 1000 can be achieved with this chemistry, and ratios around 100 are commonplace. The method allows sequential installation of a series of stereocenters and tolerates a wide variety of suitably protected functional substituents. (alpha-Amidoalkyl)boronic acids include biochemically significant serine protease inhibitors, one of which is the clinically successful proteasome inhibitor bortezomib, used for treatment of multiple myeloma and mantle cell lymphoma.

引用

页码：10009 / 10023

页数：15

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