title: alpha,beta-epoxy vinyl triflates in Pd-catalyzed reactions.
abstract: [reaction: see text] Reactions of steroidal alpha,beta-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd(0) into the C-O bond, giving vinylpalladium 12, is faster than formation of the pi-allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.
authors.affiliation: Department of Chemistry, University of California, Berkeley, 94720-1460, USA.
authors.forename: K
authors.initials: K
authors.lastname: Yamamoto
authors.forename: C H
authors.initials: CH
authors.lastname: Heathcock
mesh_terms: D000476:Alkanesulfonates / Q000138:chemical synthesis / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D008698:Mesylates / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium; D010619:Phenazines / Q000138:chemical synthesis / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000476:Alkanesulfonates; D000970:Antineoplastic Agents; D007783:Lactones; D008698:Mesylates; D010619:Phenazines; D013141:Spiro Compounds; D013256:Steroids; D010165:Palladium