Preparation of vinylglycines by thermolysis of homocysteine sulfoxides

被引：14

作者：

Patel, Sravan Kumar ^{[1
]}

Long, Timothy E. ^{[1
,2
]}

机构：

[1] Univ Georgia, Dept Pharmaceut & Biomed Sci, Athens, GA 30602 USA

[2] Univ Georgia, Ctr Drug Discovery, Athens, GA 30602 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 36期

关键词：

GLUTAMYL-GAMMA-GLUTAMATE; POTENT INHIBITORS;

D O I：

10.1016/j.tetlet.2009.06.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and efficacy of preparing Cbz-VG-OMe (1) by thermolysis of alkyl and aryl homocysteine sulfoxides were surveyed. This investigation determined that aryl sulfoxide analogs were more effective for the reaction and that the 2-nitrophenyl analog 10f possessed a unique ability to syn eliminate at temperatures as low as 100 degrees C. The thermolysis of sulfoxide 10f was additionally discovered to occur under toluene reflux and when sodium acetate was added, Cbz-VG-OMe (1) Could be obtained in high purity by simple filtration of the precipitated sulfenic acid byproduct 12. This mild protocol which was also applied in the synthesis of VC dipeptide 13 would have utility in the general synthesis of olefins and alkenes from 2-nitrophenylsulfoxides. Published by Elsevier Ltd.

引用

页码：5067 / 5070

页数：4