title: Catalytic asymmetric thiofunctionalization of unactivated alkenes.
abstract: Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States. sdenmark@illinois.edu
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.forename: David J P
authors.initials: DJ
authors.lastname: Kornfilt
authors.forename: Thomas
authors.initials: T
authors.lastname: Vogler
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D063088:Phosphoramides; D010756:Phosphoric Acids / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013455:Sulfur / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000577:Amides; D063088:Phosphoramides; D010756:Phosphoric Acids; C005438:phosphoramide; D013455:Sulfur