title: Asymmetric synthesis of (3S,1'S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one derivatives by addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones.
abstract: This paper presents the first study of the addition reactions between amide-derived nucleophiles and chiral CF3-containing N-sulfinyl-imines. We demonstrate that enolates of 1-(alkyl)-indolin-2-ones cleanly react with (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine affording 3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-ones of (3S,1'S) absolute configuration as the major reaction products with synthetically meaningful diastereoselectivity and chemical yields. The reactions were shown to be of general practical application for preparation of various oxindole derivatives in a diastereomerically pure form.
authors.affiliation: School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China. hanjl@nju.edu.cn.
authors.forename: Ping
authors.initials: P
authors.lastname: Qian
authors.forename: Chen
authors.initials: C
authors.lastname: Xie
authors.forename: Lingmin
authors.initials: L
authors.lastname: Wu
authors.forename: Haibo
authors.initials: H
authors.lastname: Mei
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
authors.forename: Jianlin
authors.initials: J
authors.lastname: Han
authors.forename: Yi
authors.initials: Y
authors.lastname: Pan
mesh_terms: D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: C000598238:(S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine; D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D013452:Sulfonium Compounds; C456900:indolin-2-one