title: Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes.
abstract: A double migratory cascade reaction of α-halogen-substituted propargylic phosphates to produce highly functionalized 1,3-dienes has been developed. This transformation features 1,3-phosphatyloxy group migration followed by 1,3-shifts of bromine and chlorine as well as the unprecedented 1,3-migration of iodine. The reaction is stereodivergent: (Z)-1,3-dienes are formed in the presence of a copper catalyst, whereas gold-catalyzed reactions exhibit inverted stereoselectivity, producing the corresponding E products.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
authors.forename: Roohollah
authors.initials: R
authors.lastname: Kazem Shiroodi
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Dudnik
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D006219:Halogens / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D006219:Halogens; D009943:Organophosphorus Compounds