title: Scandium(III)-catalyzed enantioselective allylation of isatins using allylsilanes.
abstract: The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.
authors.affiliation: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States.
authors.forename: Nadine V
authors.initials: NV
authors.lastname: Hanhan
authors.forename: Yng C
authors.initials: YC
authors.lastname: Tang
authors.forename: Ngon T
authors.initials: NT
authors.lastname: Tran
authors.forename: Annaliese K
authors.initials: AK
authors.lastname: Franz
mesh_terms: D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry; D007510:Isatin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006846:Hydrocarbons, Halogenated; D012821:Silanes; D007510:Isatin; D012538:Scandium