Improved E-selectivity in the Wittig reaction of stabilized ylides with alpha-alkoxyaldehydes and sugar lactols

Authors
Harcken, C Martin, SF
Citation
C. Harcken et Sf. Martin, Improved E-selectivity in the Wittig reaction of stabilized ylides with alpha-alkoxyaldehydes and sugar lactols, ORG LETT, 3(22), 2001, pp. 3591-3593
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
22
Year of publication
2001
Pages
3591 - 3593
Database
ISI
SICI code
1523-7060(20011101)3:22<3591:IEITWR>2.0.ZU;2-P
Abstract
[GRAPHICS] The Wittig reactions of alpha -alkoxyaldehydes and sugar lactols with stabi lized ylides such as (alkoxycarbonylmethylene)triphenylphosphoranes typical ly proceed with low E-selectivities. However, we have discovered that the r eaction of such aldehydes with (methoxycarbonylmethylene)tributylphosphoran e in toluene in the presence of catalytic amounts of benzoic acid proceeds to give the E-alpha,beta -unsaturated esters with high selectivities and in high yields.