MECHANISM AND STEREOSELECTIVITY OF INDIRECT WITTIG REACTION VIA ISOLATION OF 1,2-HYDROXYPHOSPHONIUM SALT

Authors
NISHIZAWA M KOMATSU Y GARCIA DM NOGUCHI Y IMAGAWA H YAMADA H
Citation
M. Nishizawa et al., MECHANISM AND STEREOSELECTIVITY OF INDIRECT WITTIG REACTION VIA ISOLATION OF 1,2-HYDROXYPHOSPHONIUM SALT, Tetrahedron letters, 38(7), 1997, pp. 1215-1218
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
7
Year of publication
1997
Pages
1215 - 1218
Database
ISI
SICI code
0040-4039(1997)38:7<1215:MASOIW>2.0.ZU;2-E
Abstract
An indirect Wittig reaction via isolation of a 1,2-hydroxyphosphonium salt and subsequent treatment with a base such as DBU showed identical stereoselectivity with the corresponding direct Wittig reaction at le ast between an aliphatic aldehyde and an unstable ylide. The mechanism of the indirect Wittig reaction is discussed on the basis of a synchr onous [2+2] mechanism of the Wittig reaction. (C) 1997, Elsevier Scien ce Ltd.