A Green, Enantioselective Synthesis of Warfarin for the Undergraduate Organic Laboratory

• Terence C. Wong ^[1] ; Camille M. Sultana ^[1] ; David A. Vosburg ^[1]
  1. [1] Harvey Mudd College

     Harvey Mudd College

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 87, Nº 2 (February), 2010, págs. 194-195
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • The enantioselective synthesis of drugs is of fundamental importance in the pharmaceutical industry. In this experiment, students synthesize either enantiomer of warfarin, a widely used anticoagulant, in a single step from inexpensive starting materials. Stereoselectivity is induced by a commercial organocatalyst, (R,R)- or (S,S)-1,2-diphenylethylenediamine. The environmentally friendly microscale reaction is performed at ambient temperature, and the product can be purified by recrystallization or column chromatography. Product characterization includes thin-layer chromatography, NMR spectroscopy, and polarimetry.