Improved Horner-Wadsworth-Emmons preparation of alpha-methyl- or alpha-ethyl-alpha,beta-unsaturated esters from aldehydes

Authors
Petroski, RJ Weisleder, D
Citation
Rj. Petroski et D. Weisleder, Improved Horner-Wadsworth-Emmons preparation of alpha-methyl- or alpha-ethyl-alpha,beta-unsaturated esters from aldehydes, SYN COMMUN, 31(1), 2001, pp. 89-95
Citations number
7
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
31
Issue
1
Year of publication
2001
Pages
89 - 95
Database
ISI
SICI code
0039-7911(2001)31:1<89:IHPOAO>2.0.ZU;2-6
Abstract
The E-isomer selectivity of the Horner-Wadsworth-Emmons olefination of alde hydes to form alpha -methyl- or alpha -ethyl-alpha,beta -unsaturated esters has been improved by using lithium tert-butoxide as the base, triethyl-2-p hosphonopropionate or triethyl-2-phosphonobutyrate as the phosphonate, an a ldehyde, and hexane as the reaction solvent. Greater E-isomer selectivity w as observed in the formation of alpha -methyl-alpha,beta -unsaturated eater s than alpha -ethyl-alpha,beta -unsaturated esters. These compounds are use ful intermediates for the synthesis of insect pheromones and natural produc ts.