The petasis reaction: microscale synthesis of a tertiary amine antifungal analog

• Autores: Katherine J. Koroluk, Derek A. Jackson, Andrew P. Dicks
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 89, Nº 6, 2012, págs. 796-798
• Idioma: inglés
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• Resumen

  • Students prepare a tertiary amine antifungal analog in an upper-level undergraduate organic laboratory. A microscale Petasis reaction is performed to generate a liquid compound readily characterized via IR and proton NMR spectroscopy. The biological relevance of the product is highlighted, with the tertiary amine scaffold being an important treatment option for resistant bacterial and fungal infections. The procedure allows for postlaboratory discussion of nitrogen as a stereocenter in an ammonium ion, along with principles of combinatorial chemistry and green chemistry. Deliberation of potential mechanisms for the Petasis reaction provides another valuable learning opportunity for students.