Efficient, Enantioselective Assembly of Silanediol Protease Inhibitors

被引：36

作者：

Bo, Yingjian ^{[1
]}

Singh, Swapnil ^{[1
]}

Hoan Quoc Duong ^{[1
]}

Cao, Cui ^{[1
]}

Sieburth, Scott McN ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 07期

基金：

美国国家卫生研究院;

关键词：

ASYMMETRIC CATALYSIS; PRINCIPLES; CHEMISTRY; ALCOHOLS; CARBONYL; DESIGN;

D O I：

10.1021/ol2002978

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A five-step assembly of silicon-protected dipeptide mimics from commercially available reagents is described. This methodology makes silanediol protease inhibitors readily available for the first time. The sequence features asymmetric hydrosilylation, a novel reduction of a silyl ether to a silyllithium reagent, and addition of this dianion to a sulfinimine, to produce the complete inhibitor skeleton with full control of stereochemistry. Oxidation of the primary alcohol to an acid completes the synthesis.

引用

收藏

页码：1787 / 1789

页数：3

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