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Asymmetric Synthesis of 1-Aryl-1,2-ethanediols from Arylacetylenes by Palladium-Catalyzed Asymmetric Hydrosilylation as a Key Step

Toyoshi Shimada, Kotaro Mukaide, Akihiro Shinohara, Jin Wook Han and Tamio Hayashi*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email:

T. Shimada, K. Mukaide, A. Shinohara, J. W. Han, T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584-1585.

DOI: 10.1021/ja017617g


A platinum-catalyzed hydrosilylation of arylacetylenes with trichlorosilane followed by a subsequent second hydrosilylation catalyzed by a chiral monophosphine-palladium complex and an oxidation with hydrogen peroxide gave 1-aryl-1,2-diols of high enantiomeric purity in high yields.

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Key Words

Hydrosilylation, Tamao-Fleming Oxidation, 1,2-Diols

ID: J48-Y2002-1050