104871-68-3Relevant academic research and scientific papers
Practical and highly stereoselective technology for preparation of enantiopure sulfoxides and sulfinamides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives
Han, Zhengxu,Krishnamurthy, Dhileepkumar,Grover, Paul,Fang, Q. Kevin,Su, Xiping,Wilkinson, H. Scott,Lu, Zhi-Hui,Magiera, Daniel,Senanayake, Chris H.
, p. 6386 - 6408 (2007/10/03)
A simple, general, and practical technology to prepare enantiopure 1,2,3-oxathiazolidine-2-oxide derivatives using chiral aryl N-sulfonyl aminoalcohol derivatives and thionyl chloride is reported. The versatility of these novel chiral building blocks (MIOO and TMPOO), was exemplified by the expedient production of a variety of unique chiral sulfoxides and valuable chiral sulfinamides in excellent yields and enantiopurities.
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.
