title: Anti-addition mechanism in the intramolecular hydroalkoxylation of alkenes catalyzed by PVP-stabilized nanogold.
abstract: (1R*,4S*,4aR*,9aS*,10S*)-10-Hydroxy-10-phenyl-1,4a,9a,10-tetrahydro-1,4-methanoanthracen-9(4H)-one (1c) was prepared for the elucidation of the reaction mechanism of intramolecular hydroalkoxylation of alkenes catalyzed by gold nanoclusters stabilized by a hydrophilic polymer, poly(N-vinyl-2-pyrrolidone) (Au:PVP). It was found that the reaction proceeded via anti-addition of alcohol to the alkene assisted by p-activation of the gold clusters, which is the same mechanism as the hydroamination by toluenesulfonamides.
authors.affiliation: Research Center for Molecular Scale Nanoscience, Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Kitahara
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Sakurai
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D053768:Metal Nanoparticles / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011205:Povidone / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D000475:Alkenes; D012997:Solvents; D006046:Gold; D011205:Povidone