Stereoselective synthesis of enantiomerically pure 4,5-disubstituted pyrrolidinones from beta-amino esters

Authors
Wang, JB Hou, YH Wu, P Qu, ZH Chan, ASC
Citation
Jb. Wang et al., Stereoselective synthesis of enantiomerically pure 4,5-disubstituted pyrrolidinones from beta-amino esters, TETRAHEDR-A, 10(23), 1999, pp. 4553-4561
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
23
Year of publication
1999
Pages
4553 - 4561
Database
ISI
SICI code
0957-4166(199912)10:23<4553:SSOEP4>2.0.ZU;2-8
Abstract
alpha-Alkylation of N-tosyl-protected beta-amino esters with LDA as the bas e led to high anti selectivity for the newly formed C-C bond. The alpha-alk ylated beta-amino esters were further transformed to enantiomerically pure 4,5-disubstituted pyrrolidinones through hydrolysis, diazotization, and Wol f rearrangement under AgO2CPh/Et3N/dry THF conditions. (C) 1999 Elsevier Sc ience Ltd. All rights reserved.