ANOMALOUS HORNER-WADSWORTH-EMMONS-REACTIONS ON 3,4-ENULOSES

Authors
MORADEI OM DUMORTIER CM CIRELLI AF
Citation
Om. Moradei et al., ANOMALOUS HORNER-WADSWORTH-EMMONS-REACTIONS ON 3,4-ENULOSES, Tetrahedron, 53(22), 1997, pp. 7397-7402
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
22
Year of publication
1997
Pages
7397 - 7402
Database
ISI
SICI code
0040-4020(1997)53:22<7397:AHO3>2.0.ZU;2-R
Abstract
Pyranosic enuloses were subjected to Homer-Wadswonh-Emmons (HWE) condi tions using the enolate of dimethyl(methoxycarbonyl)methyl phosphonate and its ethyl analogue 3-O-Phosphorylation of the products as well as an unusual stereoespecificity were observed. A mechanism involving a phosphonate-phosphate like rearrangement through a five member interme diate followed by benzoate elimination is proposed. (C) 1997 Elsevier Science Ltd.