Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy

• Nanette Wachter-Jurcsak ^[1] ; Kendra Reddin ^[1]
  1. [1] Hofstra University

     Hofstra University

     Town of Hempstead, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 78, Nº 9, 2001, pág. 1264
• Idioma: inglés
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• Resumen

  • We have found a beautiful example of anisochrony of diastereotopic acyclic methylene hydrogens in a symmetric diketone, synthesized by techniques traditionally performed in an introductory organic laboratory course. Synthesis of the diketone is high-yielding and easy to carry out, and the products can be directly isolated with a good degree of purity with no need of further manipulation. The reaction can be accomplished in a single laboratory session.