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A Catalytic Approach to the Metal-Free Reaction of Epoxides with Ketene Silyl Acetals for Accessing γ-Lactones

Simona Bonollo, Amanollah Zarei Ahmady, Chiara Petrucci, Assunta Marrocchi, Ferdinando Pizzo and Luigi Vaccaro*

*Laboratory of Green Synthetic Organic Chemistry, CEMIN - Dipartimento di Chimica, Biologia e Biotecnologie, UniversitÓ di Perugia Via Elce di Sotto, 8, 06123 Perugia, Italy, Email: luigi.vaccarounipg.it

S. Bonollo, A. Z. Ahmady, C. Petrucci, A. Marocchi, F. Pizzo, L. Vaccaro, Org. Lett., 2014, 16, 5721-5723.

DOI: 10.1021/ol502855q (free Supporting Information)


Abstract

Tetrabutylammonioum fluoride is a catalyst for the nucleophilic addition of silyl ketene acetals to epoxides providing γ-lactones with high regioselectivities and yields. This metal-free catalytic approach works in a very efficient manner under solvent-free conditions.

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Key Words

Lactones


ID: J54-Y2014