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
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
收藏
页码:351 / 353
页数:3
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