Borohydride Reduction of Estrone. Demonstration of Diastereoselectivity in the Undergraduate Organic Chemistry Laboratory.

• Autores: Animesh Aditya, David E. Nichols, G. Marc Loudon
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 85, Nº 11, 2008, págs. 1535-1537
• Idioma: inglés
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• Resumen

  • This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity in an undergraduate organic chemistry laboratory. Chiral hindered ketones such as estrone, undergo facile reduction with sodium borohydride in a highly diastereoselective manner. The diastereomeric estradiols produced in the reaction can be analyzed and differentiated by thin-layer chromatography and melting point.