title: Synthesis of thiazolines by copper catalyzed aminobromination of thiohydroximic acids.
abstract: A copper catalyzed aminobromination of alkene tethered thiohydroximic acids is described, providing a rapid approach to unnatural thiazoline scaffolds not readily available via existing methods. Moderate to high yields of bromothiazolines are obtained with alkyl- and aryl-substituted thiohydroximic acid building blocks containing mono-, di-, and trisubstituted alkenes. The reaction provides high levels of 5-exo selectivity, and terminally monosubstituted alkenes result in predominant syn-diastereoselectivity.
authors.affiliation: Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, United States.
authors.forename: Bérénice C
authors.initials: BC
authors.lastname: Lemercier
authors.forename: Joshua G
authors.initials: JG
authors.lastname: Pierce
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis; D000588:Amines / Q000138:chemical synthesis; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D013237:Stereoisomerism; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D000588:Amines; D006842:Hydrocarbons, Brominated; D010091:Oximes; D053778:Thiazolidines; D003300:Copper