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Molecules 2012, 17(3), 2579-2586; doi:10.3390/molecules17032579

Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold

Research Center for Molecular Scale Nanoscience, Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan
Author to whom correspondence should be addressed.
Received: 13 February 2012 / Revised: 21 February 2012 / Accepted: 22 February 2012 / Published: 2 March 2012
(This article belongs to the Special Issue Gold Catalysts)
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(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.
Keywords: gold nanoclusters; hydroalkoxylation; anti-addition; p-activation gold nanoclusters; hydroalkoxylation; anti-addition; p-activation

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Kitahara, H.; Sakurai, H. Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold. Molecules 2012, 17, 2579-2586.

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