Acylation of Ketone Silyl Enol Ethers with Acetyl Tetrafluoroborate. A Synthesis of 1,3-Diketones

Abstract

Silyl enol ethers, obtained by silylation of ketones, are acylated with acetyl tetrafluoroborate to give 1,3-diketones in reasonable yields. The tert-butyldimethylsilyl enol ether of cyclohexanone gives a nearly quantitative yield of acetylcyclohexanone, while the trimethylsilyl enol ethers of cyclohexanone and other ketones give moderate yields of the corresponding 1,3-diketones. The regiospecificity of the reaction was studied with the isomeric silyl enol ethers of 2-methylcyclohexanone. © 1981, American Chemical Society. All rights reserved.