title: Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines.
abstract: A new strategy has been established for the kinetic resolution of racemic allylic alcohols through a palladium/sulfonyl-hydrazide-catalyzed asymmetric OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2 , 4 mol % (S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcohols were smoothly resolved with selectivity factors of more than 400 through an asymmetric allylic alkylation of monosubstituted hydrazines under air at room temperature. Importantly, this kinetic resolution process provided various allylic alcohols and allylic hydrazine derivatives with high enantiopurity.
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
authors.forename: Liang
authors.initials: L
authors.lastname: Yan
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
authors.forename: Jing-Kun
authors.initials: JK
authors.lastname: Xu
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
authors.forename: Chao-Fan
authors.initials: CF
authors.lastname: Huang
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
authors.forename: Zeng-Yang
authors.initials: ZY
authors.lastname: He
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
authors.forename: Ya-Nan
authors.initials: YN
authors.lastname: Xu
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China. tiansk@ustc.edu.cn.
authors.forename: Shi-Kai
authors.identifier: http://orcid.org/0000-0002-2938-7013
authors.initials: SK
authors.lastname: Tian
keywords: alcohols; allylic compounds; kinetic resolution; palladium; sulfonyl hydrazides