Stereoselective synthesis of 2-substituted pyrrolidines

被引：15
|
作者：
Deloisy, S
Tietgen, H
Kunz, H [1 ]
机构：
[1] Univ Paris Sud, ICMO, Lab Carbocycles, F-91405 Orsay, France
[2] Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany
来源：
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2000年 / 65卷 / 05期
关键词：
carbohydrates; chiral auxiliaries; homoallylamines; electrophile-induced cyclization; pyrrolidines; nornicotine; alkaloids; enantioselective reactions;
D O I：
10.1135/cccc20000816
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Using O-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, (S) or (R) configured alpha-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced endo-trig-cyclization of these N-glycosyihomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity.
引用
收藏
页码：816 / 828
页数：13
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