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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, Email: bergmancchem.berkeley.edu, fdtosteuclink.berkeley.edu

I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc., 2003, 125, 8696-8697.

DOI: 10.1021/ja035232n (free Supporting Information)


Abstract

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.

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Key Words

β-hydroxy ketones


ID: J48-Y2003-1530