5-Methylene-2(5H)-furanone as a Dienophile in Diels-Alder Cycloadditions: Site Selectivity and Regioselectivity

Daniel Alonso, Juan Orti, Vicenc Branchadell, Antonio Oliva, Rosa M. Ortuno, Juan Bertran, Josep Font

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27 Citations (Scopus)

Abstract

Site selectivity and regioselectivity in Diels-Alder reactions of 5-methylene-2(5H)-furanone (1) with several acyclic dienes have been investigated. We have found that I consistently reacts specifically at the exocyclic double bond, giving spiro adducts in good yields. Excellent regioselectivity has also been found in either catalyzed or uncatalyzed reactions with unsymmetrically substituted dienes. A kinetic study of the reaction with isoprene has revealed that the observed regioselectivity is a direct consequence of kinetic control over the process. Theoretical calculations have been carried out in order to interpret these experimental results. © 1990, American Chemical Society. All rights reserved.
Original languageEnglish
Pages (from-to)3060-3063
JournalJournal of Organic Chemistry
Volume55
Issue number10
DOIs
Publication statusPublished - 1 Jan 1990

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