Session S41a (Tuesday, 9:30am, Wartik 110)

P390: Organocatalysis in the advanced organic laboratory

Andrea Pellerito (Indiana University, USA)

Among the objectives of an advanced organic laboratory course are the introduction of modern methods of bond formation, catalysis, and enantioselectivity.  To aid in the development of these skills, an organocatalysis lab, adapted from the chemical literature, has been developed to focus on the preparation of á-aminooxycarbonyls by using L-proline to catalyze the reaction between nitrosobenzene and an aldehyde in an enantioselective manner.  Although previously unacquainted with this class of reactions, students are able to work in groups to propose theories about the role of the small organic molecule as a catalyst and the mechanism of the reaction, including detailed discussions of the origins of enantioselectivity.  Students not only explore the role of the small organic molecule as a catalyst and the mode of asymmetric induction but also a method to complete an oxidation alpha to a carbonyl while learning the structure and reactivity of unfamiliar functional groups.


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