4.8 Article

Gold-catalyzed cyclization of allene-substituted malonate esters:: Synthesis of β,γ-unsaturated δ-lactones

Journal

ORGANIC LETTERS
Volume 9, Issue 11, Pages 2235-2237

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol070793v

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An efficient method for the preparation of beta,gamma-unsaturated delta-lactones has been developed. The starting materials for the synthesis of these compounds are allene-substituted malonates which undergo gold-catalyzed cyclization by means of nucleophilic attack of the ester moiety on the allene. It is worth mentioning that this is the first example where an ester group attacks as a nucleophile in a gold-catalyzed transformation of allenes.

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