title: Catalytic Asymmetric Ring-Opening Reactions of Aziridines with 3-Aryl-Oxindoles.
abstract: A highly enantioselective ring-opening alkylation reaction between 3-aryl-oxindole and N-(2-picolinoyl) aziridine has been realized for the first time. The reaction is efficiently mediated by a simple in-situ-generated magnesium catalyst and 3,3'-fluorinated-BINOL (BINOL=1,1'-binaphthalene-2,2'-diol) has been identified as a powerful chiral ligand. Notably, the fluorine atom on the chiral ligand plays a key role in providing the desired chiral 3-alkyl-3-aryl oxindoles with excellent enantioselectivities.
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Linqing
authors.initials: L
authors.lastname: Wang
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Dan
authors.initials: D
authors.lastname: Li
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Dongxu
authors.initials: D
authors.lastname: Yang
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Kezhou
authors.initials: K
authors.lastname: Wang
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Wang
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Pengxin
authors.initials: P
authors.lastname: Wang
authors.affiliation: Guangdong Key Laboratory of Nanomedicine, Institute of Biomedicine and Biotechnology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences, Shenzhen, Guangdong, 518055, China. wu.su@siat.ac.cn.
authors.forename: Wu
authors.initials: W
authors.lastname: Su
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China. wangrui@lzu.edu.cn.|State Key Laboratory of Chiroscience, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, P. R. China. wangrui@lzu.edu.cn.
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D007211:Indoles / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; C406944:BINOL, naphthol; D007211:Indoles; D009284:Naphthols; D000078183:Oxindoles; C022960:2-oxindole; D008274:Magnesium
keywords: 3,3′-fluorinated-binol; aziridines; magnesium catalysis; oxindoles; ring-opening reactions