title: Lewis acid promoted diastereoselective addition of TMSCN and TMSCF3 to isatin-derived N-sulfinyl ketimines: synthesis of optically active tetrasubstituted 3-aminooxindoles.
abstract: A practical and efficient method for preparation of highly enantiomerically enriched 3-cyano-3-aminooxindoles and 3-trifluoromethyl-3-aminooxindoles with up to 99% optical purity by a Lewis acid promoted diastereoselective Strecker reaction and trifluoromethylation of isatin-derived N-tert-butanesulfinyl ketimines has been developed. This protocol allows direct use of N-free isatin substrates under mild conditions.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
authors.forename: Diao
authors.initials: D
authors.lastname: Chen
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Xu
mesh_terms: D002073:Butanes / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D058428:Silica Gel / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D002073:Butanes; D003486:Cyanides; D006845:Hydrocarbons, Fluorinated; D007097:Imines; D007211:Indoles; D058116:Lewis Acids; D009570:Nitriles; D013449:Sulfonamides; D014297:Trimethylsilyl Compounds; C542835:ketimine; C511422:tert-butanesulfinamide; D058428:Silica Gel; C058010:trimethylsilyl cyanide; D007510:Isatin