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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, UniversitÓ degli Studi "La Sapienza", P.le Aldo Moro 5, 00185 Roma, Italy, Email: mauro.bassettiuniroma1.it

M. Bassetti, A. D'Annibale, A. Fanfoni, F. Minissi, Org. Lett., 2005, 7, 1805-1808.

DOI: 10.1021/ol0504087 (free Supporting Information)


Abstract

The ruthenium-catalyzed ring-closing metathesis of methallyl acrylates gave 4-Methyl-5-alkyl-2(5H)-furanones in good to high yields. Despite the electron deficiency of both double bonds in the starting acrylates, the first-generation Grubbs' catalyst proved to be an effective catalyst for the ring closure.

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Key Words

Ring-Closing Metathesis, Butenolides, Esters


ID: J54-Y2005-430