title: Kinetic resolution of primary allylic amines via palladium-catalyzed asymmetric allylic alkylation of malononitriles.
abstract: A range of primary allylic amines were resolved with selectivity factors of up to 491 through [Pd(allyl)Cl]2/(S)-BINAP-catalyzed and mesitylsulfonyl hydrazide-accelerated asymmetric allylic alkylation of malononitriles involving enantioselective C-N bond cleavage under aerobic conditions. Moreover, the reaction proved useful for the asymmetric synthesis of α-branched allyl-substituted malononitriles with high enantiopurity.
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China. ygu01@ustc.edu.cn tiansk@ustc.edu.cn.
authors.forename: Yong
authors.initials: Y
authors.lastname: Wang
authors.forename: Ya-Nan
authors.initials: YN
authors.lastname: Xu
authors.forename: Guo-Sheng
authors.initials: GS
authors.lastname: Fang
authors.forename: Hong-Jian
authors.initials: HJ
authors.lastname: Kang
authors.forename: Yonghong
authors.initials: Y
authors.lastname: Gu
authors.forename: Shi-Kai
authors.initials: SK
authors.lastname: Tian
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry; D007700:Kinetics; D009570:Nitriles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000588:Amines; D006834:Hydrazines; D009570:Nitriles; D012997:Solvents; C029424:hydrazine; D010165:Palladium