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. 2012 Mar 2;17(3):2579-86.
doi: 10.3390/molecules17032579.

Anti-addition mechanism in the intramolecular hydroalkoxylation of alkenes catalyzed by PVP-stabilized nanogold

Hiroaki Kitahara  1 , Hidehiro Sakurai
Affiliations

Anti-addition mechanism in the intramolecular hydroalkoxylation of alkenes catalyzed by PVP-stabilized nanogold

Hiroaki Kitahara et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
Possible mechanism of Au:PVP-catalyzed hydroalkoxylation of γ-hydroxyalkenes (1).
Scheme 2
Scheme 2
Two possible route to intramolecular hydroamination.
Scheme 3
Scheme 3
Preparation of γ-hydroxyalkene 1c.
Scheme 4
Scheme 4
Anti-Addition mechanism in the Au:PVP-catalyzed hydroalkoxylation.
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