A total stereospecific route to alpha-alkylidene-gamma-lactams

Authors
Beji, F Lebreton, J Villieras, J Amri, H
Citation
F. Beji et al., A total stereospecific route to alpha-alkylidene-gamma-lactams, TETRAHEDRON, 57(50), 2001, pp. 9959-9962
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
50
Year of publication
2001
Pages
9959 - 9962
Database
ISI
SICI code
0040-4020(200112)57:50<9959:ATSRTA>2.0.ZU;2-A
Abstract
A new efficient gamma -lactams 4 synthesis was achieved by two successive r eactions: alkylation of nitroalkane anions with dimethyl alpha-(bromomethyl ) fumarate 1 leading to the formation of (E)-1-alkyl-2,3-dimethoxycarbonyl butadienes 3a,b resulting of tandem alkylation-elimination (dehydronitratio n) processes, followed by an intramolecular cyclization on addition of prim ary amine. (C) 2001 Published by Elsevier Science Ltd.