Interview with Jennifer M. Schomaker

Jennifer M. Schomaker

Professor Schomaker began her research career as a college freshman at Dow Chemical in Organic Chemicals and Polymers, later moving to a full-time position in Agricultural Chemicals Process Research, where she participated in route selection and scale-up campaigns for two new herbicides. During her employment, she completed her B.S. and M.S. degrees in Chemistry, then left Dow to attend graduate school at Michigan State University, where she obtained her Ph.D. in 2006 with Prof. Babak Borhan. She then moved to UC-Berkeley as an NIH postdoctoral fellow with Prof. Robert G. Bergman and F. Dean Toste. Since 2009, she has been Professor of Chemistry at the University of Wisconsin-Madison. Her awards include the NSF-CAREER, Sloan Research Fellowship, Thieme Chemistry Journal Award, ACS-WCC Rising Star Award, ACS DOC Early Academic Investigator Award, MSU Distinguished Alumni Award, and the UW-Vilas Mid-Career and UW2020 Awards. She was named a 2016 Kavli Fellow and received a 2019 Gabor A. and Judith K. Somorjai Miller Visiting Professor Award at Berkeley. She is the author of over 100 papers and patents. Research in the Schomaker group spans a broad range of interests, inspired by early efforts to solve challenges hampering the study of densely functionalized, stereochemically complex amine-containing natural products that bind to the ribosome, as well as explore new amine chemical space. In this context, we developed a suite of versatile oxidative allene amination tools to prepare diverse analogues of known bioactive molecules and identify new sp^3 nitrogen-containing scaffolds with activities against malaria, tuberculosis, and cancer. Our design of a new class of cycloalkynes for cell labeling studies, where the polarizability of the alkyne is tunable to achieve bioorthogonality with a variety of coupling partners, has opened up opportunities for exciting collaborations. Our interest in catalyst-controlled C–H functionalization led us to describe the first examples of controlling the diverse coordination geometry of silver-supported nitrenes to achieve chemo-, site- and enantioselective amidations of a range of diverse C–H bonds.

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What inspired you to choose science and eventually become a chemist in the first place?

Having completed all available science courses in my first two years of high school, I was fortunate to have dedicated STEM teachers who offered me numerous opportunities to carry out independent projects. I realized learning went far beyond the material in textbooks, gained the confidence to recognize failure was just a step on the way to success, and experienced the thrill of designing and analyzing my own experiments. I hope I convey this same enthusiasm to my own students at all levels!

What do you think are the most interesting parts of your research work?

The ability to work in academia has provided my students and I with myriad opportunities to move outside our scientific comfort zones. While I still rely on my training in synthesis and methods development, the ability to apply these skills to address problems across a broad range of disciplines is one of the most interesting aspects of my work. When I started at Wisconsin, I never envisaged we would computationally design silver catalysts for tunable nitrene transfer, develop new bioorthogonal labeling reagents, or work on molecules for light-activated electrophysiology. The twists and turns provided by a research-based career have been both immensely challenging and rewarding!

How do you usually spend your time outside research work?

Our family loves nature and spending time out-of-doors, so I can usually be found hiking, canoeing, climbing, gardening, or biking when I′m not at work. I find many of my best ideas occur to me when I′m relaxed and free to think only about science.

What are your suggestions for the younger generation to encourage them to consider a career in science?

On a societal level, pursuing a career in science gives one the necessary tools to productively address a host of challenges that impact our world, from clean water, food production, human health, renewable energy, and beyond. On a personal level, having a career where learning, discovery, and exercise of creativity are everyday occurrences is one of the most satisfying that I can imagine. In addition, the chance to work with talented colleagues from all over the world and across many disciplines provide continual intellectual and personal growth.

References

1. M. Ju, M. Huang, L. E. Vine, J. M. Roberts, M. Dehghany and J. M. Schomaker, Tunable, catalyst-controlled syntheses of β- and γ-amino alcohol motifs enabled by silver complexes, Nat. Catal., 2019, 2, 899–908.
2. K. A. Nicastri, J. Eshon, S. C. Schmid, W. Raskop, I. A. Guzei, I. Fernández and J. M. Schomaker, Intermolecular [3 + 3] Ring-Expansion of Aziridines to Dehydropiperidines through the Intermediacy of Aziridinium Ylides, Nat. Commun., 2019 , under review.
3. S. C. Schmid, I. A. Guzei, I. Fernández and J. M. Schomaker, Ring expansion of bicyclic methyleneaziridines via concerted, near-barrierless [2,3]-Stevens rearrangements of aziridinium ylides, ACS Catal., 2018, 8, 7907–7914.
4. M. Huang, T. Yang, J. Paretsky, J. F. Berry and J. M. Schomaker, Inverting Steric Effects: Using ‘Attractive’ Non-Covalent Interactions to Direct Silver-Catalyzed Nitrene Transfer, J. Am. Chem. Soc., 2017, 139, 17376–17386.
5. S. C. Schmid and J. M. Schomaker, A Stereoselective Ring Expansion of the Synthesis of Highly-Substituted Methylene Azetidines, Angew. Chem., Int. Ed., 2017, 56, 12229–12233.
6. M. Ju, C. D. Weatherly, I. A. Guzei and J. M. Schomaker, Chemo- and enantioselective silver-catalyzed aziridinations, Angew. Chem., Int. Ed., 2017, 56, 9944–9948.
7. E. G. Burke, B. Gold, T. T. Hoang, R. T. Raines and J. M. Schomaker, Fine-tuning Strain and Electronic Activation of Strain-promoted 1,3-Dipolar Cycloaddition with Endocyclic Sulfamates in SNO-OCTs, J. Am. Chem. Soc., 2017, 139, 8029–8037.
8. N. Dolan, R. Scamp, T. Yang, J. F. Berry and J. M. Schomaker, Catalyst-controlled and tunable, chemoselective silver-catalyzed intermolecular nitrene transfer: Experimental and computational studies, J. Am. Chem. Soc., 2016, 138, 14658–14667.
9. R. Van Hoveln, B. Hudson, H. Wedler, D. M. Bates, G. Le Gros, D. Tantillo and J. M. Schomaker, Experimental and Computational Insights into the Mechanism of Cu-catalyzed 1,3-Halogen Migration, J. Am. Chem. Soc., 2015, 137, 5346–5354.
10. R. Scamp, J. M. Alderson, A. M. Phelps, N. Dolan and J. M. Schomaker, Ligand-controlled, tunable silver-catalyzed C-H amination, J. Am. Chem. Soc., 2014, 136, 16720–16723.
11. J. W. Rigoli, C. D. Weatherly, J. M. Alderson, B. Vo and J. M. Schomaker, Tunable, Chemoselective Amination via, Silver Catalysis, J. Am. Chem. Soc., 2013, 135, 17238–17241.
12. R. D. Grigg, R. Van Hoveln and J. M. Schomaker, Cu-catalyzed recycling of halogen activating groups via 1,3-halogen migration, J. Am. Chem. Soc., 2012, 134, 16131–16134.
13. C. S. Adams, L. A. Boralsky, I. A. Guzei and J. M. Schomaker, Modular functionalization of allenes to aminated stereotriads, J. Am. Chem. Soc., 2012, 134, 10807–10810.

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