DIASTEREOSELECTIVE AND ENANTIOSELECTIVE INTRAMOLECULAR AMINO-ZINC-ENOLATE CARBOMETALATION REACTIONS - A NEW POLYSUBSTITUTED PYRROLIDINES SYNTHESIS

Authors
LORTHIOIS E MAREK I NORMANT JF
Citation
E. Lorthiois et al., DIASTEREOSELECTIVE AND ENANTIOSELECTIVE INTRAMOLECULAR AMINO-ZINC-ENOLATE CARBOMETALATION REACTIONS - A NEW POLYSUBSTITUTED PYRROLIDINES SYNTHESIS, Journal of organic chemistry, 63(8), 1998, pp. 2442-2450
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
8
Year of publication
1998
Pages
2442 - 2450
Database
ISI
SICI code
0022-3263(1998)63:8<2442:DAEIA>2.0.ZU;2-T
Abstract
The amino-zinc-enolate cyclization allowed a new and straightforward r oute to polysubstituted pyrrolidines from simple starting materials. F rom this study, we have been able to determine, for the first time, th e stereochemical influence of the substituents on the ring in the carb ocyclization reaction. The diastereoselectivity thus obtained was expl ained by a chairlike amino-zinc-enolate transition state.