The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory

• Christopher J. Nichols ^[1] ; Melissa R. Taylor ^[1]
  1. [1] California State University, United States
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 82, Nº 1, 2005, pág. 105
• Idioma: inglés
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• Resumen

  • A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.