Organocatalytic Enantioselective 1,4-Addition as a Capstone Experiment in Organic Chemistry

We have developed a capstone experiment involving the enantioselective 1,4-addition between N,N-dimethyl-m-anisidine to crotonaldehyde in the presence of an imidazolidinone organocatalyst. The exercise exposes students to contemporary areas of research while utilizing reactions commonly seen in the sophomore organic chemistry sequence. We emphasize the significance of enantioselective organic transformations and the relevance of this area of research to the pharmaceutical industry. We present the exercise as an alternative to methods requiring the use of air sensitive and expensive reagents like transition metal catalysts; the availability and ease-of-use of organocatalysts make them ideal for use in the undergraduate laboratory.