Organic reactions in water: Indium mediated synthesis of alpha-alkylidene-beta-lactams

Authors
Jayaraman, M Batista, MT Manhas, MS Bose, AK
Citation
M. Jayaraman et al., Organic reactions in water: Indium mediated synthesis of alpha-alkylidene-beta-lactams, HETEROCYCLE, 49, 1998, pp. 97-100
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
49
Year of publication
1998
Pages
97 - 100
Database
ISI
SICI code
0385-5414(199812)49:<97:ORIWIM>2.0.ZU;2-N
Abstract
Indium mediated Barbier type addition of allyl bromides to azetidine-2,3-di ones (1) in aqueous media provided two homoallylic alcohols (for example, 2 and 3) which on mesylation followed by elimination in the presence of DBU gave a mixture of E and Z isomers of alpha-alkylidene-beta-lactams (4 and 5 ) in excellent yield. These highly substituted beta-lactams are versatile s ynthons for a variety of structures.