title: Brønsted acid catalyzed phosphoramidic acid additions to alkenes: diastereo- and enantioselective halogenative cyclizations for the synthesis of C- and P-chiral phosphoramidates.
abstract: The first highly diastereo- and enantioselective additions of a halogen and phosphoramidic acid to unactivated alkenes have been developed, catalyzed by a chiral Brønsted acid. A unique feature of these additions is the opportunity for stereocontrol at two noncontiguous chiral centers, carbon and phosphorus, leading to cyclic P-chiral phosphoramidates. In addition to their inherent value, the phosphoramidates are precursors to enantioenriched epoxy allylamines.
authors.affiliation: Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Toda
authors.forename: Maren
authors.initials: M
authors.lastname: Pink
authors.forename: Jeffrey N
authors.initials: JN
authors.lastname: Johnston
mesh_terms: D000143:Acids / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000143:Acids; D000475:Alkenes; D000577:Amides; D010756:Phosphoric Acids; C011067:phosphoramidic acid