The focus of this research involves the use of tert-butanesulfinamide chemistry for the efficient, stereoselective synthesis of complex amines. The goals of the project will include using metal-catalyzed additions of boron species to amines; exploring additions to alpha, beta-unsaturated N-sulfinyl imines; developing reactions of N-sulfinyl metalloenamines with Michael acceptors with subsequent transformations upon the Michael addition products; characterizing and studying applications of N-sulfinyl aldemine self-condensation; using N-sulfinyl amidines in the synthesis of densely functionalized amines, including the asymmetric synthesis of natural products and; developing an enhanced understanding of the dynamic kinetic resolution of sulfinyl halides for the preparation of a broad range of sulfinate esters, sulfoxides and sulfinamides.
With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research and educational activities of Dr. Jonathan A. Ellman in the Department of Chemistry at the University of California, Berkeley. Professor Ellman will focus his work on developing methods for preparation of highly functionalized chiral amines using tert-butanesulfinamide chemistry. The new methodology will be integrated into the asymmetric synthesis of relevant natural products. Since over 75% of all drugs and drug candidates contain amine functionality, this project has important broader impacts for the pharmaceutical and biotechnology industries. Also, the project will offer excellent training to both undergraduate and graduate students.
