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

页码：816 / 828

页数：13

共 28 条

[1]

[Anonymous], 1985, BIOCH ALKALOIDS

[2]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[3]

2-E

[4]

Arend M., 1998, ANGEW CHEM, V110, P1096, DOI DOI 10.1002/(SICI)1521-3757(19980420)110:8