A Conversation with Dr. Anne McNeil: Celebrating 20 Years of Beckman Scholars

AMBF: Prior to college, were you curious about a career in science?

Anne McNeil (AM): As a kid, I was always very interested in learning as much as I could about the natural world around me. This meant frequent play outside where I could perform my own “experiments” with nature. As such, I always knew that I would eventually pursue a career in science, though I did not have any idea what that actually meant or would look like. I just wanted to keep learning and refining my understanding of the natural world.

AMBF: What exposure did you have to knowing what research in a laboratory would be like?
AM: To me, labs were the hands-on activities we did in high school (e.g., rolling a ball down an incline). I really had no idea of what “research” was nor did I grasp how close the frontiers of each discipline could be to me if I got started in research.

AMBF: When you heard about the Beckman Scholar opportunity, what inspired you to apply?
AM: I had literally just started my first research experience when I heard about the Beckman Scholarship. I was loving every second in the lab and was excited about the opportunity to be able to continue working in the same lab over the next 1.5 years. I was also excited by the additional mentoring that went along with the fellowship, where I got to meet weekly with the other fellowship recipients and practice giving talks, sharing our research joys and frustrations, and delving into deeper topics like ethics. Last, I had heard that this scholarship would involve travel to a national symposium and I was excited by the opportunity to meet other students from across the country.

AMBF: What was your research focused on? What were the results?
AM: The original focus of the work was aimed at preparing highly reactive reagents for C–C bond forming reactions – a transformation that is widely utilized in organic synthesis. During the course of this research, however, an older student observed that these highly reactive reagents were unstable and decomposed over the course of a few hours. The products that formed and how they formed them turned out to be even more interesting research question, and one that I pursued with my Beckman Scholarship. My work focused on elucidating the products of that decomposition reaction and the mechanism by which they formed. The preliminary results suggested that the reaction proceeded through a vinyl carbocation intermediate. At the time, there was a controversy in the chemistry literature about whether (or not) this high-energy intermediate could even exist. Our initial results suggested “yes” and we published this work before I graduated:

Primary Vinyl Cations in Solution: Kinetics and Products of α,α-Disubstituted Alkenyl(aryl)iodonium Triflate Fragmentations. Robert J. Hinkle, Anne J. McNeil, Quinn A. Thomas, and Marie N. Andrews J. Am. Chem. Soc. 1999,121, 7437-7438.

My mentor and additional students expanded this initial work and refined the mechanistic hypothesis further and reported those results in a second paper, published after I graduated:

Vinyl Carbocations: Solution Studies of Alkenyl(aryl)iodonium Triflate Fragmentations. Anne J. McNeil, Robert J. Hinkle, E. Ashley Rouse, Quinn A. Thomas, and David B. Thomas J. Org. Chem. 2001, 66, 5556-5565

AMBF: What was the most memorable part about working with your mentor or working in the laboratory?
AM: The benefits of this long-term research experience with the samementor and in the same department were enormous. I was able to establish close friendships with my peers, the other faculty in my department, as well as my mentor. It was a comfortable place to learn, make mistakes, and grow. My PI was a scientific “father figure,” and I looked to him for advice on everything. He was very involved in our lives, eating lunch with us once a week, taking frequent hiking trips, and even just going out to a dinner or playing softball now and then. At the same time, he had very high expectations of himself and worked hard, which inspired me to set high expectations for myself and work hard to meet them. Working in a research laboratory was incredibly addictive for me (in a good way). I was driven to come in each day because each day brought new data that had not been collected or analyzed before by ANYONE! It was exhilarating to be the one who uncovers something new.

AMBF: Where did you go after graduation?
AM: I matriculated into the graduate program in Chemistry at Cornell University, where I later earned my PhD working with David Collum.

AMBF: Did you continue doing scientific research?
AM: Yes. My research was focused on elucidating the structure (and reactivity) of a different class of reactive intermediates (lithium enolates) that are useful for making C­–C bonds in organic synthesis. I’ve published 7 papers on this topic:

Liou, L. R.; McNeil, A. J.; Toombes, G. E. S.; Collum, D. B. Structures of β-Amino Ester Enolates: New Strategies using the Method of Continuous Variation. J. Am. Chem. Soc. 2008, 130, 17334–17341.

Gruver, J. M.; Liou, L. R.; McNeil, A. J.; Ramírez, A.; Collum, D. B. Solution Structures of Lithium Enolates, Phenolates, Carboxylates, and Alkoxides in the Presence of N,N,N’,N’-Tetramethylethylenediamine: A Prevalence of Cyclic Dimers. J. Org. Chem. 2008, 73, 7743–7747.

Liou, L. R.; McNeil, A. J.; Ramírez, A.; Toombes, G. E. S.; Gruver, J. M.; Collum, D. B. Lithium Enolates of Simple Ketones: Structure Determination Using the Method of Continuous Variation. J. Am. Chem. Soc. 2008, 130, 4859–4868.

Collum, D. B.; McNeil, A. J.; Ramírez, A. Lithium Diisopropylamide: Solution Kinetics and Implications for Organic Synthesis. Angew. Chem. Int. Ed. 2007, 46, 3002–3017.

McNeil, A. J.; Collum, D. B. Reversible Enolization of β-Amino Carboxamides by Lithium Hexamethyldisilazide. J. Am. Chem. Soc.2005, 127, 5655–5661.

McNeil, A. J.; Toombes, G. E. S.; Gruner, S. M.; Lobkovsky, E.; Collum, D. B.; Chandramouli, S. V.; Vanasse, B. J.; Ayers, T. A. Diastereoselective Alkylation of β-Amino Esters: Structural and Rate Studies Reveal Alkylations of Hexameric Lithium Enolates. J. Am. Chem. Soc. 2004, 126, 16559–16568.

McNeil, A. J.; Toombes, G. E. S.; Chandramouli, S. V.; Vanasse, B. J.; Ayers, T. A.; O'Brien, M. K.; Lobkovsky, E.; Gruner, S. M.; Marohn, J. A.; Collum, D. B. Characterization of β-Amino Ester Enolates as Hexamers via6Li NMR Spectroscopy. J. Am. Chem. Soc. 2004, 126, 5938–5939.

AMBF: What effect did the Beckman Scholar experience have on your career?
AM: The BSP catapulted my career in science and research. Each day I would learn something new, and learn where the edge of our understanding is within the field. It was at the same time both overwhelming and exciting. I still feel the same way now. The Beckman Scholarship was the single biggest factor that set me on my life path to a career in scientific research. The additional mentoring and networking that the fellowship provided was the icing on the already quite delicious cake. One of my fondest memories is actually getting to meet Arnold Beckman at the Symposium and personally thank him for supporting me.

AMBF: Do you have any advice for undergraduates considering a research career?
AM: Absolutely! I tell all the undergraduates that I teach to get involved in “real” research during their time at UM. I tell them that you never know if you will get hooked (or not) until you start asking fundamental research questions and come up with your own ideas. As much as I’ve tried to make our teaching labs more “research-like,” there is no comparison to an authentic research experience.