Phosphine-catalyzed hydration and hydroalkoxylation of activated olefins: use of a strong nucleophile to generate a strong base.

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 beta-hydroxy and beta-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.

• Publication year

  2003

• Venue

  Journal of the American Chemical Society

• Publication date

  2003-06-18

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/JA035232NPMID 12862443
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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