A DIASTEREOSELECTIVE APPROACH TO ENANTIOPURE 3-SUBSTITUTED PYRROLIDINES FROM MASKED LITHIUM HOMOENOLATES DERIVED FROM NOREPHEDRINE

Authors
GARCIAVALVERDE M PEDROSA R VICENTE M GARCIAGRANDA S GUTIERREZRODRIGUEZ A
Citation
M. Garciavalverde et al., A DIASTEREOSELECTIVE APPROACH TO ENANTIOPURE 3-SUBSTITUTED PYRROLIDINES FROM MASKED LITHIUM HOMOENOLATES DERIVED FROM NOREPHEDRINE, Tetrahedron, 52(32), 1996, pp. 10761-10770
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
32
Year of publication
1996
Pages
10761 - 10770
Database
ISI
SICI code
0040-4020(1996)52:32<10761:ADATE3>2.0.ZU;2-6
Abstract
N-Alkoxycarbonyl-2-(2'-bromoethyl)oxazolidines derived from norephedri nes are transformed into lithium derivatives by reaction with 1 or 2 e quiv of tert-butyllithium in Et(2)O. The lithium intermediates readily cyclize to bicyclic lactams that react with acetaldehyde and benzalde hyde leading to the addition products in excellent chemical yields and moderate diastereoselectivities. Removal of the chiral appendage prov ides enantiopure 3-substituted pyrrolidines. Copyright (C) 1996 Elsevi er Science Ltd