AN EASY ACCESS TO PROTECTED (4S, 5R)-5-ALKYL-4-HYDROXY-2-PYRROLIDINONES AND THEIR USE AS VERSATILE SYNTHETIC INTERMEDIATES

Authors
HUANG PQ WANG SL YE JL RUAN YP HUANG YQ ZHENG H GAO JX
Citation
Pq. Huang et al., AN EASY ACCESS TO PROTECTED (4S, 5R)-5-ALKYL-4-HYDROXY-2-PYRROLIDINONES AND THEIR USE AS VERSATILE SYNTHETIC INTERMEDIATES, Tetrahedron, 54(41), 1998, pp. 12547-12560
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
41
Year of publication
1998
Pages
12547 - 12560
Database
ISI
SICI code
0040-4020(1998)54:41<12547:AEATP(>2.0.ZU;2-R
Abstract
A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2-pyrro lidinones is described. The key steps involve a regioselective Grignar d reagent addition to (S)-malimides, and diastereoselective reductive dehydroxylation of the resulting hemi-azaketals. The flexibility of th is methodology has been demonstrated by the synthesis of (2R, 3R)3-ami no-1 -benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, and the unnatural enantiomer of the beta-hydroxy-ga mma-amino acid residue of hapalosin in lactam form. (C) 1998 Elsevier Science Ltd. All rights reserved.