Diastereoselective synthesis of alpha-butadienyl-beta-lactams and some stereochemical aspects of their Diels-Alder adducts

Authors
Sharma, AK Kumar, RS Mahajan, MP
Citation
Ak. Sharma et al., Diastereoselective synthesis of alpha-butadienyl-beta-lactams and some stereochemical aspects of their Diels-Alder adducts, HETEROCYCLE, 52(2), 2000, pp. 603-619
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
2
Year of publication
2000
Pages
603 - 619
Database
ISI
SICI code
0385-5414(20000201)52:2<603:DSOAAS>2.0.ZU;2-J
Abstract
An efficient diastereoselective synthesis of alpha-dienyl-beta-lactams via [2+2] cycloadditions of imines with butadienyl ketene is reported. The dien yl functionality of alpha-dienyl-beta-lactams was then exploited in Diels-A lder reactions with N-phenylmaleimide (NPM), diethyl fumarate (DEF), ethyl acrylate (EA), 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and stereochemica l aspects of their Diels-Alder adducts are reported.