A new synthetic route to beta-unsubstituted beta-lactones by intramolecular cyclization

Authors
Alexandre, FR Legoupy, S Huet, F
Citation
Fr. Alexandre et al., A new synthetic route to beta-unsubstituted beta-lactones by intramolecular cyclization, TETRAHEDRON, 56(24), 2000, pp. 3921-3926
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
24
Year of publication
2000
Pages
3921 - 3926
Database
ISI
SICI code
0040-4020(20000609)56:24<3921:ANSRTB>2.0.ZU;2-H
Abstract
When carboxylic acids beta-substituted by a tert-butoxy group were treated with thionyl chloride, an intermediate acyl chloride beta-substituted by a hydroxyl group was likely formed. Its subsequent intramolecular cyclization produced novel beta-lactones in one step. Two enantiomerically enriched la ctones could be prepared via intermediates obtained by enzymatic hydrolysis . (C) 2000 Elsevier Science Ltd. All rights reserved.