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
- 5 January 1986
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 15 (1) , 65-68
- https://doi.org/10.1246/cl.1986.65
Abstract
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% stereospecificity at the sulfur atom. This method was applicable smoothly to enol silyl ethers of other cyclic ketones with high stereospecificity.This publication has 3 references indexed in Scilit:
- Enantiospecific lactonizations of chiral 1-(arylsulfinyl)cyclohexenes with chloro ketenesJournal of the American Chemical Society, 1984
- .alpha.-Sulfenylated carbonyl compounds in organic synthesisChemical Reviews, 1978
- Chemistry of carbanions. XVIII. Preparation of trimethylsilyl enol ethersThe Journal of Organic Chemistry, 1969