A catalytic approach to the metal-free reaction of epoxides with ketene silyl acetals for accessing γ-lactones.

Org Lett

Laboratory of Green Synthetic Organic Chemistry, CEMIN - Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia Via Elce di Sotto, 8, 06123 Perugia, Italy.

Published: November 2014

The first catalytic approach to the nucleophilic addition of silyl ketene acetals 2 to epoxides 1 is reported. The defined protocol is metal-free using tetrabutylammonioum fluoride as the catalyst. It works in a very efficient manner under solvent-free conditions (SolFC) allowing γ-lactones 3 to be directly obtained with high regioselectivities and yields.

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Source
http://dx.doi.org/10.1021/ol502855qDOI Listing

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