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

2004/03/16 by Joshua J. Kennedy‐Smith, Steven T. Staben, F. Dean Toste · 6 citations
Chemistry · #Catalytic Alkyne Reactions #Catalytic C–H Functionalization Methods #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja049487s

openalex publication_date 2004/03/16 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/24

Abstract

The intramolecular addition of beta-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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• Catalytic Enantioselective Conia-Ene Reaction
• Gold(I)-Catalyzed Stereoselective Olefin Cyclopropanation
• Gold(I)‐Catalyzed Cyclizations of Silyl Enol Ethers: Application to the Synthesis of (+)‐Lycopladine A
• Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes
• Conia-ene reaction [wikipedia]