title: Synthesis of enantiopure tert-butanesulfinamide from tert-butanesulfinyloxazolidinone.
abstract: A three-step procedure for the preparation of enantiopure tert-butanesulfinamide 6 in 51% overall yield is described starting from (1R,2S)-N-Cbz-1,2-diphenylaminoethanol. The key step is the reaction of tert-butylmagnesium chloride with N-Cbz-4,5-diphenyl-1,2,3-oxathiazolidine-2-oxide 2 to afford the optical pure tert-butylsulfinyl-4,5-diphenyl-1,3-oxazolidinone 5 via an 1,5-alkoxy anion rearrangement, which is then subject to ammonia hydrolysis with LiNH(2) in liquid ammonia to give (R)-tert-butanesulfinamide 6.
authors.affiliation: Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China. yanshuqin@yahoo.com
authors.forename: Yong
authors.initials: Y
authors.lastname: Qin
authors.forename: Canhui
authors.initials: C
authors.lastname: Wang
authors.forename: Zhiyan
authors.initials: Z
authors.lastname: Huang
authors.forename: Xue
authors.initials: X
authors.lastname: Xiao
authors.forename: Yaozhong
authors.initials: Y
authors.lastname: Jiang