Nathan A. Stasko - Honors in Chemistry
Metal Ligand Catalysis for the Baylis-Hillman Reaction


A new catalyst was prepared for the Baylis-Hillman reaction from 3-aminoquinuclidine and 4-methoxybenzoyl urea. Complexation of a metal by the tethered molecule provides a Lewis-acid catalyst to activate p-nitrobenzaldehyde for attack by ethyl acrylate. The rate of the Baylis-Hillman reaction was compared to the rate of standard DABCO catalyst. Results were evaluated based on a model of an intra-molecular Lewis-acid catalyst.