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Synlett 1995; 1995(5): 431-433
DOI: 10.1055/s-1995-4991
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Easy Access to Optically Pure Functionalized γ-Alkylated Lactones starting from (2R, 3R)-Tartaric Acid

Anne-Marie Fernandez, Marc Jacob, Jean Gralak, Yashar Al-Bayati, Gérard Plé, Lucette Duhamel*
  • *Université de Rouen, URA CNRS DO 464 and IRCOF, F-76821 Mont-Saint-Aignan Cedex (France). Fax: (33)-35-14-66-70
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Publication History

Publication Date:
31 December 2000 (online)

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Protected and deprotected γ-alkylated dihydroxylactones 8 and 1 are prepared from (2R,3R)-tartaric acid. The key step is the highly diastereoselective reduction of ketones 6 using sodium borohydride in methanol at low temperature.

γ-alkylated lactones - tartaric acid - highly stereoselective reduction