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A convenient method for the preparation of α-vinylfurans by phosphine-initiated reactions of various substituted enynes bearing a carbonyl group with aldehydes
Authors:Hirofumi Kuroda  Emi Hanaki  Hironori Izawa  Michiko Kano  Hiromi Itahashi
Affiliation:Department of Chemical and Biochemical Engineering, Toyama National College of Technology, 13 Hongo-machi, Toyama-shi, Toyama 939-8630, Japan
Abstract:α-Vinylfurans were obtained by phosphine-initiated cyclization of various enynes bearing a carbonyl group at the ene end in the presence of various aldehydes, in moderate to high yields. The reaction may consist of 1,6-addition of phosphine to the enynes, ring closure, and Wittig reaction between the ylid resulting from cyclization and an aldehyde. Thus, various aldehydes were able to be used in the reaction. The reaction was influenced greatly by the substituents at the acetylene position (R1) and the α-position of the carbonyl group (R3).
Keywords:Cyclization   Vinyl furans   Enynes   Phosphine   Wittig reaction
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