Special Houk-Jung Organic Colloquium 247: Dr. Alistair Sterling

When
January 17, 2023 4:00 pm - 5:00 pm
Where
Mani L. Bhaumik Centennial Collaboratory
607 Charles E. Young Dr., East
Los Angeles, CA 90095 United States
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Speaker Dr. Alistair Sterling

Description

Strain is a foundational concept in organic chemistry. Its presence can transform an inert molecule into one with exciting properties, or steer a reaction toward a single product with exquisite control. Understanding—and importantly, predicting—the delicate balance between strain and reactivity will enable the full potential of strain to be harnessed for drug discovery, materials chemistry, bioconjugation and beyond. In this talk, efforts to uncover the fundamental principles that govern strain release chemistry will be discussed, using the highly-strained hydrocarbon [1.1.1]propellane to develop the concept of bond delocalization,1 before demonstrating how this idea can be generalized to predict the behaviour of all small-ring carbocycles.2 The implications of this interplay between strain, bonding and reactivity will be explored through reaction development built upon halogen bonding and photoredox catalysis,3,4 offering guidelines to develop reactions that capitalize on strain release reactivity.5

[1] Sterling, A. J., Dürr, A. B., Smith, R. C., Anderson, E. A., Duarte, F., Chem. Sci. 2020, 11, 4895–4903.

[2] Sterling, A. J., Smith, R. C., Anderson, E. A., Duarte, F., ChemRxiv 2021 (https://doi.org/10.26434/chemrxiv-2021-n0xm9).

[3] Livesly, S., Sterling, A. J., Robertson, C. C., Goundry, W., Morris, J. A., Duarte, F., Aïssa, C., Angew. Chem. Int. Ed. 2022, 61, e202111291.

[4] Wong, M. L. J., Sterling, A. J., Mousseau, J. J., Duarte, F., Anderson, E. A., Nat. Commun. 2021, 12, 1644.

[5] Frank, N., Nugent, J., Shire, B. R., Pickford, H. D., Rabe, P., Sterling, A. J., Zarganes-Tzitzikas, T., Grimes, T., Thompson, A. L., Smith, R. C., Schofield, C. J., Brennan, P. E., Duarte, F., Anderson, E. A., Nature 2022, 611, 721–726.

Dr. Alistair Sterling

Dr. Alistair Sterling is a computational organic chemist interested in uncovering the origins of chemical reactivity for the design of new reactions, pharmaceuticals and materials. He received his MChem Chemistry degree in 2017 from the University of Oxford (UK), where he spent a year in the group of Prof. Edward Anderson working on the total synthesis of polyene natural products. He received his DPhil in Organic Chemistry from the University of Oxford in 2021, working between the groups of Profs. Fernanda Duarte and Edward Anderson and supported by an Oxford-Radcliffe scholarship. During this time, Alistair worked on the use of computation to develop strain release chemistry for drug discovery, alongside projects spanning physical organic chemistry, synthetic reaction development, and transmembrane anion transport. He was subsequently awarded the EPSRC Doctoral Prize in 2021, spending six months in Oxford as a Postdoctoral Research Associate before moving to Berkeley, California, where he is currently a Postdoctoral Scholar at the Lawrence Berkeley National Lab and the University of California, Berkeley (USA). Alistair’s current research in the group of Prof. Martin Head-Gordon focuses on the development of theoretical tools to understand chemical bonding for the design of C–H functionalization catalysts.