Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

Abstract

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.

Keywords

• alkylation
• gold catalysis
• leaving group
• silyl enol ether
• substitution reaction