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Gold(I)-Catalyzed Conia-Ene Reaction of β-Ketoesters with Alkynes

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Joshua J. Kennedy-Smith, Steven T. Staben, and F. Dean Toste*

Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720

J. Am. Chem. Soc., 2004, 126 (14), pp 4526–4527

DOI: 10.1021/ja049487s

Publication Date (Web): March 16, 2004

Section:

Alicyclic Compounds

Abstract

The intramolecular addition of β-ketoesters to unactivated alkynes under neutral conditions and at room temperature is described. The method employs triphenylphosphinegold(I) cation as a catalyst for the formation of exo-methylenecycloalkanes. Both monocyclic and bicyclic cyclopentanes and cyclohexanes can be formed in excellent yields and with good diastereoselectivity.

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