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
J. Am. Chem. Soc., 2002, 124 (8), pp 1584–1585
DOI: 10.1021/ja017617g
Publication Date (Web): February 20, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

Double hydrosilylation of arylacetylenes with trichlorosilane catalyzed first by platinum and second by a chiral monophosphine−palladium complex generated the corresponding 1,2-bis(silyl)-1-arylethanes, the oxidation of which with hydrogen peroxide gave 1-aryl-1,2-diols of high enantiomeric purity (94−98% ee) in high yields.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue February 27, 2002
  • Received November 27, 2001
    Revised January 8, 2002

Recommend & Share

Related Content

Other ACS content by these authors: