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Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-unsaturated Lactones

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2013 Aug 3
PMID 23905884
Citations 7
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Abstract

AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted α,β-unsaturated-γ-lactones in 55-98% yields. This method was also applicable to the synthesis of α,β-unsaturated-δ-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the α-bromo-substituted α,β-unsaturated lactones.

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