Synthesis of α,β-Unsaturated 4,5-Disubstituted γ-Lactones via Ring-Closing Metathesis Catalyzed by the First-Generation Grubbs' Catalyst

Mauro Bassetti,*† Andrea D'Annibale,*‡ Alessia Fanfoni, and Franco Minissi;
Istituto CNR di Metodologie Chimiche, Sezione Meccanismi di Reazione, Dipartimento di Chimica, Universit degli Studi La Sapienza, P.le Aldo Moro 5, 00185 Roma, Italy, and Dipartimento di Chimica, and Istituto CNR di Chimica Biomolecolare, Sezione di Roma, Universit degli Studi La Sapienza, P.le Aldo Moro 5, 00185 Roma, Italy
Org. Lett., 2005, 7 (9), pp 1805–1808
DOI: 10.1021/ol0504087
Publication Date (Web): April 2, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Istituto CNR di Metodologie Chimiche.

,
‡

 Dipartimento di Chimica, Università “La Sapienza”.

, mauro.bassetti@uniroma1.it, ; , andrea.dannibale@uniroma1.it

Abstract

Abstract Image

4-Methyl-5-alkyl-2(5H)-furanones have been prepared by ruthenium-catalyzed ring-closing metathesis of the suitable methallyl acrylates. Despite the electron deficiency of the conjugated double bond and of the gem-disubstitution of the allylic alkene moiety in the starting acrylates, the first-generation Grubbs' catalyst I proved to be an effective promoter for the ring closure, affording the expected butenolides in good to high yields.

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History

  • Published In Issue April 28, 2005
  • Received February 24, 2005

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