title: Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.
abstract: A Rh(III)-catalyzed C-H bond addition/primary amine-promoted cyclization of bis-Michael acceptors is reported. The C-H bond addition step occurs with high chemoselectivity, and the subsequent intramolecular Michael addition, mediated by a primary amine catalyst, sets three contiguous stereocenters with high diastereoselectivity. A broad range of directing groups and both aromatic and alkenyl C-H bonds were shown to be effective in this transformation, affording functionalized piperidines, tetrahydropyrans, and cyclohexanes.
authors.affiliation: Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8170, United States.
authors.forename: Tyler J
authors.initials: TJ
authors.lastname: Potter
authors.affiliation: Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8170, United States.
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000588:Amines; D003510:Cyclohexanes; D010880:Piperidines; D011714:Pyrans; D012238:Rhodium