Stereoselective synthesis of 2-substituted pyrrolidines

Authors
Deloisy, S Tietgen, H Kunz, H
Citation
S. Deloisy et al., Stereoselective synthesis of 2-substituted pyrrolidines, COLL CZECH, 65(5), 2000, pp. 816-828
Citations number
27
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
00100765 → ACNP
Volume
65
Issue
5
Year of publication
2000
Pages
816 - 828
Database
ISI
SICI code
0010-0765(200005)65:5<816:SSO2P>2.0.ZU;2-Z
Abstract
Using O-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylam ine, (S) or (R) configured alpha-substituted homoallylamines are synthesize d 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.