- California Institute of Technology
1200 E. California Blvd.
M/C 101-20
Pasadena, CA 91125 - 614-406-3610
- I was born in central Ohio and attended the Ohio State University, where I graduated with a B.S. in Chemistry in 2010. I moved east to pursue my graduate studies working with Prof. David MacMillan at Princeton University pursuing new conceptual developments in the field of Photoredox Catalysis. ... moreI was born in central Ohio and attended the Ohio State University, where I graduated with a B.S. in Chemistry in 2010. I moved east to pursue my graduate studies working with Prof. David MacMillan at Princeton University pursuing new conceptual developments in the field of Photoredox Catalysis. After defending my thesis in October of 2015, I moved to the west coast to work as a Postdoctoral Researcher with Prof. Brian Stoltz at Caltech pursuing the total synthesis of the anticancer alkaloid Jorumycin.
My research interests lie in organic synthesis, specifically as the field continues to expand and merge with the physical and biological sciences. During my Ph.D. I was involved in a collaboration with Prof. Jim McCusker's group at Michigan State University to study the photophysical processes that were enabling a transformation I had developed in the MacMillan group. As a postdoc, I am currently involved in a collaboration with Prof. Dennis Slamon's group at UCLA for the biological evaluation of jorumycin and its derivatives. I believe that organic synthesis is at its best when it is able to incorporate concepts from other fields to enable new modes of reactivity.
I firmly believe that the ideal research group welcomes students of all backgrounds, nationalities, races, and genders and gender expressions. My aspiration is to lead a research group focused on the development of new concepts in catalysis and in the synthesis of biologically active natural products that embraces these ideals.edit
The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong gram-positive and -negative antibiotic... more
The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong gram-positive and -negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet-Spengler reaction, that mimics their biosynthetic pathways. Herein we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of non-natural analogs.
Research Interests:
Transition metal catalysis has traditionally relied on organometallic complexes that can cycle through a series of ground-state oxidation levels to achieve a series of discrete yet fundamental fragment-coupling steps. The viability of... more
Transition metal catalysis has traditionally relied on organometallic complexes that can cycle through a series of ground-state oxidation levels to achieve a series of discrete
yet fundamental fragment-coupling steps. The viability of excited-state organometallic catalysis via direct photoexcitation has been demonstrated. Although the utility of triplet sensitization by energy transfer has long been known as a powerful activation mode in organic photochemistry, it is surprising to recognize that photosensitization mechanisms to access excited-state organometallic catalysts have lagged far behind. Here, we demonstrate excited-state organometallic catalysis via such an activation pathway: Energy transfer from an iridium sensitizer produces an excited-state nickel complex that couples aryl halides with carboxylic acids. Detailed mechanistic studies confirm the role of photosensitization via energy transfer.
yet fundamental fragment-coupling steps. The viability of excited-state organometallic catalysis via direct photoexcitation has been demonstrated. Although the utility of triplet sensitization by energy transfer has long been known as a powerful activation mode in organic photochemistry, it is surprising to recognize that photosensitization mechanisms to access excited-state organometallic catalysts have lagged far behind. Here, we demonstrate excited-state organometallic catalysis via such an activation pathway: Energy transfer from an iridium sensitizer produces an excited-state nickel complex that couples aryl halides with carboxylic acids. Detailed mechanistic studies confirm the role of photosensitization via energy transfer.
Research Interests:
The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet... more
The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (–)-bursehernin.
Research Interests:
Stereoconvergent catalysis is an important subset of asymmetric synthesis that encompasses stereoablative transformations, dynamic kinetic resolutions, and dynamic kinetic asymmetric transformations. Initially, only enzymes were known to... more
Stereoconvergent catalysis is an important subset of asymmetric synthesis that encompasses stereoablative transformations, dynamic kinetic resolutions, and dynamic kinetic asymmetric transformations. Initially, only enzymes were known to catalyze dynamic kinetic processes, but recently various synthetic catalysts have been developed. This Review summarizes major advances in nonenzymatic, transition-metal-promoted dynamic asymmetric transformations reported between 2005 and 2015.
Research Interests:
A method for the preparation of indazoles is described. Oximes derived from 2-aminoacetophenone derivatives are mesylated, resulting in the direct formation of indazoles in a simple and high-yielding process.