Source: Vy M. Dong and Faben Cruz, Department of Chemistry, University of California, Irvine, CA

This experiment will demonstrate the concept of organocatalysis by illustrating the proper setup of a reaction that utilizes enamine catalysis. Organocatalysis is a form of catalysis that uses substoichiometric amounts of small organic molecules to accelerate reactions. This type of catalysis is complementary to other forms of catalysis such as transition metal or biocatalysis. Transition metal catalysis involves transition metals as catalysts and biocatalysis uses enzymes as catalysts. Some advantages of organocatalysis include the low toxicity and cost of the organocatalysts in comparison to many metal catalysts. In addition, most organocatalysts are not sensitive to air and moisture, unlike metal catalysts. In contrast to enzymes found in living organisms, the small molecules that act as organocatalysts are typically easy to access. Furthermore, organocatalysis offers complementary and new reactivity not observed with other forms of catalysis.

1. Add (S)-proline (40 mg, 0.35 mmol, 0.35 equivalents), acetonitrile (MeCN, 5 mL), and the diketone (126 mg, 1 mmol, 1 equivalent) to a round-bottom flask (~ 20 mL) equipped with a magnetic stir bar.
2. Stir the reaction mixture at 35 °C for 30 min.
3. Add 3-buten-2-one (105 mg, 1.5 mmol, 1.5 equivalents) dropwise at 35 °C and stir at the same temperature for 1 week.
4. Cool the reaction to room temperat

The purified product should have the following ¹H NMR spectrum: ¹H NMR δ 5.88 (1H, s), 2.6-2.7 (2H, m), 2.3-2.55 (4H, m), 2.0-2.2 (2H, m), 1.6-1.8 (2H, m), 1.4 (3H, s).

This experiment has demonstrated how to set up an enamine catalyzed reaction. Compared to other forms of catalysis, organocatalysis is a relatively young field of research, but in recent years the field of organocatalysis has experienced dramatic growth. The increased interest in organocatalysis has also given rise to research that makes use of more than one type of catalysis to achieve new types of reactivity. For example, there has been increased reports of using organocatalysis in conjunction with transition metal cat