title: A highly diastereoselective Friedel-Crafts reaction of indoles with isatin-derived N-sulfinyl ketimines towards the efficient synthesis of chiral tetrasubstituted 3-indolyl-3-aminooxindoles.
abstract: A Lewis acid promoted highly diastereoselective asymmetric Friedel-Crafts alkylation of indoles with isatin-derived N-tert-butanesulfinyl ketimines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Bi(OTf)3, providing a series of 3-indolyl-3-aminooxindoles in excellent diastereoselectivities (up to 98% de) and yields (up to 99%).
authors: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. xumh@simm.ac.cn.
authors: Jian-Ping
authors: JP
authors: Chen
authors: Wen-Wen
authors: WW
authors: Chen
authors: Yi
authors: Y
authors: Li
authors: Ming-Hua
authors: MH
authors: Xu
mesh_terms: D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines; D007211:Indoles; D009570:Nitriles; C542835:ketimine; D007510:Isatin