Organic chemistry is an enabling science, providing access to much-needed molecules for the treatment of disease, development of new materials and devices, and investigation of biochemical pathways. It also enables insight into the molecular level interactions that define our world. An ongoing cha
llenge in organic chemistry is the discovery of efficient methods to synthesize target molecules. In particular, the preparation of chiral molecules as single enantiomers is crucial for biological and biomedical applications. Towards the goal of highly efficient methods, the use of transition metal catalysts to provide both reactivity and selectivity has transformed the way that organic molecules are constructed.
Our research program is directed towards harnessing the power of transition metal catalysts to enable new, efficient methods for the preparation of chiral molecules in highly enantioenriched form. In particular, we are discovering transition metal-catalyzed reactions of electrophiles that are not typically used with these catalysts. With this approach, we seek solutions to long-standing challenges in the synthesis of enantioenriched organic molecules, which are vital for the study and treatment of human disease.
Stereospecific Cross Couplings of Amine- and Alcohol-derived Electrophiles
Recognizing that highly enantioenriched amine and alcohol derivatives are widely available and thus ideal substrates for stereospecific cross couplings, we have a program to develop cross couplings of these electrophiles with air-stable, functional group tolerant partners. Our efforts have resulted in multiple new methods to transform carbon–nitrogen and carbon–oxygen bonds into carbon–carbon and carbon–boron bonds in valuable product molecules with both tertiary and quaternary stereocenters.
Enantioselective, Copper-Catalyzed Additions to Cationic Intermediates Ions
Oxygen and nitrogen heterocycles with α-stereocenters constitute an important scaffold in a number of bioactive molecules. A powerful approach to their synthesis is enantioselective addition to cyclic oxocarbenium ions, which are easily formed in situ from widely available acetal precursors. Recognizing the wealth of precedent in the catalytic generation of a wide variety of chiral organometallic nucleophiles, we are developing copper-catalyzed alkynylation of oxocarbenium and iminium ions. Our methods enable high yields and enantioselectivities in the synthesis of a variety of heterocyclic products.
Please see our Publications page for more information.