Phosphine-Mediated Reductive Condensation of γ-Acyloxy Butynoates: A Diversity Oriented Strategy for the Construction of Substituted Furans
- 11 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (13) , 4118-4119
- https://doi.org/10.1021/ja049377l
Abstract
Exposure of γ-acyloxy butynoates to stoichiometric quantities of triphenylphosphine results in reductive condensation to afford substituted furans, by way of allenic ester intermediates. As γ-acyloxy butynoates are readily obtained through condensation of ethyl propiolate with aldehydes followed by acylation, this method represents a powerful and mechanistically novel protocol for the convergent three-component construction of substituted furans.Keywords
This publication has 9 references indexed in Scilit:
- A convenient method for the preparation of furans by the phosphine-initiated reactions of enynes bearing a carbonyl groupTetrahedron Letters, 1999
- Regioselective syntheses of substituted furansTetrahedron, 1998
- The natural products chemistry of West Indian gorgonian octocoralsTetrahedron, 1995
- A mild method for the synthesis of furans. Application to 2,5-bridged furano macrocyclic compoundsThe Journal of Organic Chemistry, 1990
- Five-membered heteroaromatic rings as intermediates in organic synthesisChemical Reviews, 1986
- Flash vacuum thermolysis of β-keto-trimethylsilyl-enol-ethersTetrahedron, 1982
- Oxyphosphoranes with an oxaphospholene ring: analysis of the activation barriers of the isomerization processJournal of the American Chemical Society, 1981
- Alkaline cleavage reactions of tetraalkylphosphonium saltsJournal of the American Chemical Society, 1973
- Nuclear magnetic resonance evidence for the pathways of pseudorotation in alkyloxyphosphoranesJournal of the American Chemical Society, 1970