title: Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: reaction development and applications.
abstract: We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.
authors.affiliation: Department of Chemistry, Stanford University, Stanford University, CA 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Yong
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry* / Q000378:metabolism; D000078183:Oxindoles; D010830:Physostigmine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D006846:Hydrocarbons, Halogenated; D007211:Indoles; D000078183:Oxindoles; C483283:communesin B; C090331:debromoflustramine B; C472225:perophoramidine; C022960:2-oxindole; D008982:Molybdenum; D010830:Physostigmine; C092280:phenserine