title: Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions for the Synthesis of Cyclic Sulfamides.
abstract: The synthesis of cyclic sulfamides by enantioselective Pd-catalyzed alkene carboamination reactions between N-allylsulfamides and aryl or alkenyl bromides is described. High levels of asymmetric induction (up to 95:5 e.r.) are achieved using a catalyst composed of [Pd2 (dba)3 ] and (S)-Siphos-PE. Deuterium-labelling studies indicate the reactions proceed through syn-aminopalladation of the alkene and suggest that the control of syn- versus anti-aminopalladation pathways is important for asymmetric induction.
authors.affiliation: Department of Chemistry, University of Michigan, 930. N. University Ave., Ann Arbor, MI, 48109-1055, USA.
authors.forename: Zachary J
authors.initials: ZJ
authors.lastname: Garlets
authors.affiliation: Department of Chemistry, University of Michigan, 930. N. University Ave., Ann Arbor, MI, 48109-1055, USA.
authors.forename: Kaia R
authors.initials: KR
authors.lastname: Parenti
authors.affiliation: Department of Chemistry, University of Michigan, 930. N. University Ave., Ann Arbor, MI, 48109-1055, USA. jpwolfe@umich.edu.
authors.forename: John P
authors.identifier: http://orcid.org/0000-0002-7538-6273
authors.initials: JP
authors.lastname: Wolfe
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003903:Deuterium / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D013449:Sulfonamides; D010165:Palladium; D003903:Deuterium
keywords: asymmetric catalysis; enantioselective; heterocycles; palladium; sulfamides