Alkaloid-Derived Thioureas in Asymmetric Organocatalysis: A Cooperative Learning Activity in a Project-Based Laboratory Course

• David Monge ^[1]
  1. [1] Universidad de Sevilla

     Universidad de Sevilla

     Sevilla, España

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 92, Nº 8, 2015, págs. 1390-1393
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • An experiment carried out by advanced undergraduate students in a project-based laboratory course is described. Taking into account the positive effects of working in teams, which has been key for successful research in industry and academia, a cooperative learning experience in the laboratory was developed. Students working in teams of four synthesize two alkaloid-derived thioureas starting from a chiral pool (quinidine and quinine). The thioureas are used to catalyze an enantioselective Michael reaction between acetylacetone and trans-4-methyl-β-nitrostyrene, providing a platform for discussion of stereochemistry and chirality transfer events. Qualitative analysis of the reaction enantioselectivity is performed by polarimetry, which allows students to assign product optical rotations (+/−) with their absolute configurations (S/R). Students are exposed to an entire research process: analysis of primary literature, discussion with colleagues, planning laboratory schedules, and execution of experiments.