Synthesis of highly substituted pyrrolidines via palladium-catalyzed cyclization of 5-vinyloxazolidinones and activated alkenes

被引：28

作者：

Knight, Julian G. ^{[1
]}

Stoker, Paul A. ^{[1
]}

Tchabanenko, Kirill ^{[1
]}

Harwood, Simon J. ^{[2
]}

Lawrie, Kenneth W. M. ^{[2
]}

机构：

[1] Newcastle Univ, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[2] GlaxoSmithKline Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON | 2008年 / 64卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tet.2008.02.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Tosyl-5,5-divinyloxazolidin-2-one undergoes a palladium-catalyzed decarboxylative cyclization across a range of electrophilic alkenes to give the corresponding pyrrolidine derivatives bearing two contiguous quaternary centres. Alkenes bearing two electron-withdrawing groups are required; pyrrolidines were not formed from mono-activated alkenes. Bulky, electron-rich phosphines promote pyrrolidine formation with less highly electrophilic, doubly activated alkenes, and a dramatic improvement is observed in the presence of iodide. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3744 / 3750

页数：7

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