A Multistep Organocatalysis Experiment for the Undergraduate Organic Laboratory: An Enantioselective Aldol Reaction Catalyzed by Methyl Prolinamide

Abstract

In recent years, there has been an explosion of research concerning the area of organocatalysis. A multistep capstone laboratory project that combines traditional reactions frequently found in organic laboratory curriculums with this new field of research is described. In this experiment, the students synthesize a prolinamide-based organocatalyst that is then used to perform an enantioselective aldol reaction between acetone and 4-nitrobenzaldehyde. The enantiomeric excess (ee) of the reaction is determined by chiral HPLC and polarimetry. Students obtained ee values ranging from 46 to 59%. This experiment is designed to be adaptable and can be performed with minimal equipment (glassware, IR, and polarimeter). It also provides flexibility to the instructor, due to the wide range of topics that may be emphasized in the experience.