The unifying theme of our research is the discovery and application of new reactions for organic synthesis.  Many of the transformations we target are based on common structural motifs or functional group patterns present in molecules provided to us by nature.

Nickel–Catalyzed Carbon–Carbon Bond Formation.  The majority of the transformations under investigation are carbon–carbon bond–forming reactions promoted by nickel catalysts. We have discovered a variety of coupling reactions to join a number of different functional groups in highly regio–, stereo– and enantioselective fashion depending on the nature of the supporting ligands on nickel. 

Epoxide–Opening Cascades.  Over two decades ago, Koji Nakanishi proposed a provocative explanation for the structural and stereochemical similarities found across the ladder polyether family of natural products – the transformation of a polyepoxide into a ladder polyether via a cascade of epoxide–opening events. An ongoing effort in our group is the replication or emulation of such cascades. One aim is the efficient synthesis of these extremely complex natural products. In addition, we hope that our explorations into a diverse set of epoxide–opening cyclizations and cascades will shed further light on the fundamental feasibility of the Nakanishi’s hypothesis.

Target–Oriented Synthesis.  In order to test the scope and the utility of newly developed methods, we strive to employ them in the total synthesis of natural products. Often these products are the original inspiration for the development of these methods. For example, we have found that nickel–catalyzed reactions are compatible with a wide array of functional groups, making them useful in complex settings, such as fragment coupling or macrocyclization operations at a late stage in synthesis.

• Ng, S.–S.; Ho, C.–Y.; Schleicher, K. D.; Jamison, T. F. “Nickel–Catalyzed Coupling Reactions of Alkenes,” Pure Appl. Chem. 2008, 80, 929.

• Vilotijevic, I.; Jamison, T. F. “Epoxide–Opening Cascades Promoted by Water,” Science 2007, 317, 1189.

• Moslin, R. M.; Jamison, T. F. “Highly Convergent Total Synthesis of (+)–Acutiphycin,” J. Am. Chem. Soc. 2006, 128, 15106.

• Ng., S.–S.; Ho, C.–Y.; Jamison, T. F. “Nickel–Catalyzed Coupling of Alkenes, Aldehydes, and Silyl Triflates,” J. Am. Chem. Soc. 2006, 128, 11513.

• Simpson, G. L.; Heffron, T. P.; Merino, E.; Jamison, T. F. “Ladder Polyether Synthesis via Epoxide–Opening Cascades Using a Disappearing Directing Group,” J. Am. Chem. Soc. 2006, 128, 1056.

• Colby, E. A.; O’Brien, K. C.; Jamison, T. F. “Total Syntheses of Amphidinolide T1 and T4 via Catalytic, Stereoselective Reductive Macrocyclizations,” J. Am. Chem. Soc. 2005, 127, 4297.