(Z)-dimethyl alpha-(bromomethyl)fumarate, an efficient intermediate for the selective synthesis of dimethyl 3-alkyl itaconates and 2-alkyl 3-carbomethoxy-gamma-lactams

Authors
Beltaief, I Besbes, R Ben Amor, F Amri, H Villieras, J Villieras, J
Citation
I. Beltaief et al., (Z)-dimethyl alpha-(bromomethyl)fumarate, an efficient intermediate for the selective synthesis of dimethyl 3-alkyl itaconates and 2-alkyl 3-carbomethoxy-gamma-lactams, TETRAHEDRON, 55(13), 1999, pp. 3949-3958
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
13
Year of publication
1999
Pages
3949 - 3958
Database
ISI
SICI code
0040-4020(19990326)55:13<3949:(AAEIF>2.0.ZU;2-V
Abstract
(Z)-Dimethyl alpha-(bromomethyl)fumarate 2 proved to be an efficient precur sor of 3-substituted itaconic acid esters 3 via its reaction with magnesium dialkylcuprates. Some hindered esters 3 can be used for the diastereoselec tive synthesis of alpha-alkylated-beta-methoxycarbonyl-gamma-lactams 6. (C) 1999 Elsevier Science Ltd. All rights reserved.