Enzymatic Resolution of (+/-)-Menthol Using Transesterification with Methyl (2R)-(+)-2-Chloropropanoate:: A Biocatalyzed Reaction Studied by NMR Spectroscopy and Polarimetry for an Advanced Undergraduate Project in Modern Organic Chemistry

• C. Poiré ^[1] ; C. Rabiller ^[1] ; C. Chon ^[1] ; P. Hudhomme ^[1]
  1. [1] University of Nantes

     University of Nantes

     Arrondissement de Nantes, Francia

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 73, Nº 1 (January), 1996, págs. 93-95
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • Lipase from Candida rugosa is used as an efficient biocatalyst for the kinetic resolution of (+/-)-Menthol. Methyl (2R)-(+)-2-chloropropanoate is chosen as an acyl donor for the transesterification reaction of menthol. Candida rugosa lipase catalyzes this transformation only with the (-)-menthol thus providing the corresponding 2-chloropropanoate with an excellent diastereomeric excess (>94%). This reaction is a part of an integrated laboratory project in stereoselective organic synthesis for advanced undergraduate students in the University of Nantes (France).