Tandem silylformylation/Wittig olefination of terminal alkynes: Stereoselective synthesis of 2,4-dienoic esters

Authors
Eilbracht, P Hollmann, C Schmidt, AM Barfacker, L
Citation
P. Eilbracht et al., Tandem silylformylation/Wittig olefination of terminal alkynes: Stereoselective synthesis of 2,4-dienoic esters, EUR J ORG C, (7), 2000, pp. 1131-1135
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
7
Year of publication
2000
Pages
1131 - 1135
Database
ISI
SICI code
1434-193X(200004):7<1131:TSOOTA>2.0.ZU;2-7
Abstract
The rhodium(I)-catalysed sequential silylformylation/Wittig olefination of terminal alkynes with hydrosilanes and carbon monoxide in the presence of s tabilised P-ylides leads to substituted 2,4-dienoic esters in a one-pot pro cedure. The alpha,beta,gamma,delta-unsaturated esters are generated with hi gh (2E,4Z) stereoselectivity in good to excellent yields. Conversions of th e products in [2+1] cycloaddition reactions are presented.