3-(PROP-2-ENYLIDENE)AZETIDIN-2-ONE DERIVATIVES - SYNTHESIS, STRUCTURE, AND FORMATION OF 3-SPIRO-BETA-LACTAMS VIA DIELS-ALDER REACTIONS

Authors
RUF S OTTO HH
Citation
S. Ruf et Hh. Otto, 3-(PROP-2-ENYLIDENE)AZETIDIN-2-ONE DERIVATIVES - SYNTHESIS, STRUCTURE, AND FORMATION OF 3-SPIRO-BETA-LACTAMS VIA DIELS-ALDER REACTIONS, Helvetica Chimica Acta, 78(3), 1995, pp. 629-635
Citations number
14
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
78
Issue
3
Year of publication
1995
Pages
629 - 635
Database
ISI
SICI code
0018-019X(1995)78:3<629:3D-SS>2.0.ZU;2-A
Abstract
Reactions of 3-silylated beta-lactams (1) with alpha,beta-unsaturated ketones give the propylidene-beta-lactams 3 and the cycloalkenylidene derivatives 5. Structure and configuration are elucidated by spectrosc opic methods, and the reactivity is discussed. While compounds 5 do no t react with dienophiles, the (Z)-isomers of 3 are the favored substra tes for Diels-Alder reactions yielding the spiro compounds 6 and 7.