Regio- and stereoselectivity in the cyclization of enolates derived from 4,5-, 5,6-, and 6,7-epoxy-1-phenyl-1-alkanones. Competition between C- and O-alkylation

Authors
Crotti, P Di Bussolo, V Favero, L Macchia, F Pineschi, M Napolitano, E
Citation
P. Crotti et al., Regio- and stereoselectivity in the cyclization of enolates derived from 4,5-, 5,6-, and 6,7-epoxy-1-phenyl-1-alkanones. Competition between C- and O-alkylation, TETRAHEDRON, 55(18), 1999, pp. 5853-5866
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
18
Year of publication
1999
Pages
5853 - 5866
Database
ISI
SICI code
0040-4020(19990430)55:18<5853:RASITC>2.0.ZU;2-5
Abstract
The results obtained in the base-catalyzed intramolecular cyclization of en olates derived from some representative 4,5-, 5,6-, and 6,7-epoxy ketones a nd of the corresponding alkenes are discussed. The LHMDS/Sc(OTf)(3) protoco l on epoxy ketones appears to be a valuable tool for the stereoselective ob tainment of the corresponding cyclic gamma-hydroxy ketones (gamma-HKs). (C) 1999 Elsevier Science Ltd. All rights reserved.