Diastereoselective synthesis of cis-2,5-disubstituted pyrrolidine N-oxides by the retro-Cope elimination

被引：8

作者：

Bagley, MC ^{[1
]}

Tovey, J ^{[1
]}

机构：

[1] Univ Wales Coll Cardiff, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 02期

关键词：

Cope elimination; cyclisation; diastereoselection; nitrones; N-oxides; pyrrolidines;

D O I：

10.1016/S0040-4039(00)01964-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrones were reacted with 3-butenylmagnesium bromide to give alkenylhydroxylamines that were cyclised by retro-Cope elimination. Heating the diastereomeric mixtures of pyrrolidine N-oxides in the absence of solvent affected a highly diastereoselective isomerisation to provide the cis-2,5-disubstituted products in excellent yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：351 / 353

页数：3