104792-08-7Relevant academic research and scientific papers
A NOVEL AND USEFUL SYNTHETIC WAY TO CHIRAL α-SULFINYL CYCLIC KETONES BY THE ACID-CATALYZED REACTION OF ENOL SILYL ETHERS OF CYCLIC KETONES WITH CHIRAL SULFINATES
Horio, Kunio,Matsuyama, Nobuhiko
, p. 65 - 68 (2007/10/02)
The acid-catalyzed reactions of enol silyl ethers of cyclic ketones with chiral sulfinic esters provided a new and general entry to optically active α-sulfinyl ketones.Reaction of the enol silyl ether of cyclohexanone with methyl (S)-p-toluenesulfinate in the presence of boron trifluoride etherate (2.0 equiv.) produced (RS)-2-p-toluenesulfinylcyclohexanone with inversion of configuration in 98.3 percent stereospecifity at the sulfur atom.This method was applicable smoothly to enol silyl ethers of other cyclic ketones with high stereospecifity.
