Phosphine-Catalyzed Hydration and Hydroalkoxylation of Activated Olefins:  Use of a Strong Nucleophile to Generate a Strong Base

Ian C. Stewart, Robert G. Bergman,* and F. Dean Toste*;
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720
J. Am. Chem. Soc., 2003, 125 (29), pp 8696–8697
DOI: 10.1021/ja035232n
Publication Date (Web): June 18, 2003
Copyright © 2003 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.

, bergman@cchem.berkeley.edu, ; , fdtoste@uclink.berkeley.edu

Abstract

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The direct addition of water and a variety of alcohols to activated olefins was observed in the presence of nucleophilic phosphine catalysts. Unlike existing methods, the reactions proceed at room temperature and in the absence of transition metals, or strong acids or bases. The use of simple commercially available catalysts makes this an attractive method for the preparation of β-hydroxy and β-alkoxy substrates, which are prevalent targets and intermediates in organic synthesis. The scope and mechanism of this reaction has been explored, and the compound that acts as the resting state of the catalyst was synthesized independently. Our mechanism also suggests the possibility of extending the scope of this reactivity to other classes of nucleophiles.

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History

  • Published In Issue July 23, 2003
  • Received March 19, 2003

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