title: Enantioselective N-alkylation of isatins and synthesis of chiral N-alkylated indoles.
abstract: Asymmetric N-alkylations of isatins with enals were shown to be feasible via a prolinol-catalyzed iminium activation, and N-alkylated isatins were obtained in good yields and with excellent enantioselectivity. The biologically useful N-alkylated isatins also served as valuable synthetic precursors, and could be readily converted to chiral N-alkylated indole derivatives. The described method provides a novel entry to access optically enriched N-alkylated isatins and indole derivatives.
authors.affiliation: Department of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore 117543. chmlyx@nus.edu.sg.
authors.forename: Xiaowei
authors.initials: X
authors.lastname: Dou
authors.forename: Weijun
authors.initials: W
authors.lastname: Yao
authors.forename: Chunhui
authors.initials: C
authors.lastname: Jiang
authors.forename: Yixin
authors.initials: Y
authors.lastname: Lu
mesh_terms: D000478:Alkylation; D002384:Catalysis; D007097:Imines; D007211:Indoles / Q000138:chemical synthesis*; D007510:Isatin / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism
chemical_list: D007097:Imines; D007211:Indoles; D007510:Isatin