Shuming Chen

  • Assistant Professor of Chemistry and Biochemistry

Areas of Study

Education

  • BA, Grinnell College, 2011
  • PhD, Yale University, 2016

From detergents to painkillers, from Retina Displays to Eco Boxes – the quality of modern human life is sustained by an endless supply of chemical compounds produced through organic synthesis. Organic synthesis involves rearranging the way atoms are connected to each other. Orchestrating this dance of atoms requires chemists to strike a fine balance between aggressiveness and precision, for even a seemingly trivial difference in the connection, orientation or spatial arrangement of atoms can mean the difference between a life-saving drug and a life-ruining poison. As such, efficient synthesis of organic compounds requires the development of processes that are selective for products with the desired atomic connection, orientation, as well as three-dimensional shape.

Despite the importance of chemical selectivity, the key to controlling it is often shrouded in mystery. Chemical reactions typically take place on time scales measured in femtoseconds (quadrillionths of a second), via even more fleeting structures dubbed transition states. While transition states are energetic bottlenecks that typically control the selectivity of reactions, they are exceedingly difficult to study by experimental means. Fortunately, modern computational chemistry has risen to the task and enabled chemists to obtain molecular-level insight into these transient but all-important structures. The overarching goal of my research is to leverage the synergy of computation and experiment to discover what drives chemical selectivity. The mechanistic insight we generate is in turn used to guide the design of reactions that are more selective, efficient and environmentally-friendly.

Students in my lab have the opportunity to learn the following experimental and computational techniques:

Experimental - organic and inorganic synthesis (including air- and water-free techniques such as glove boxes and Schlenk line usage), NMR spectroscopy (including heteronuclear NMR and specialized air-free NMR techniques), LCMS/GCMS, column chromatography, preparatory thin-layer chromatography, X-ray single crystal growth

Computational - Density Functional Theory (DFT) calculations (using Gaussian software), quasiclassical molecular dynamics (MD) simulations, reaction mechanism elucidation, automated conformational searches, Python scripting for data analysis (for students with more CS background)

Visit Prof. Chen's group website to learn more.

Oberlin undergraduate student coauthors are underlined:

• Ji, P.; Davies, C. C.; Gao, F.; Chen, J.; Meng, X.; Houk, K. N.*; Chen, S.*; Wang, W.* Selective Skeletal Editing of Polycyclic Arenes Using Organophotoredox Dearomative Functionalization. Nat. Comm.2022, 13, 4565.

• Han, F.; Choi, P. H.; Ye, C.-X.; Grell, Y.; Xie, X.; Ivlev, S. I.; Chen, S.*; Meggers, E.* Cyclometalated Chiral-at-Ruthenium Catalyst for Enantioselective Ring-Closing C(sp3)–H Carbene Insertion to Access Chiral Flavanones. ACS Catal. 2022, 12, 10304.

• Kazerouni, A. M.; Brandes, D. S.; Davies, C. C.; Cotter, L. F.; Mayer, J. M.*; Chen, S.*; Ellman, J. A.* Visible Light-Mediated, Highly Diastereoselective Epimerization of Lactams from the Most Accessible to the More Stable Stereoisomer. ACS Catal.2022, 12, 7798.

• Lv, L.*; Qian, H.; Crowell, A. B.; Chen, S.*; Li, Z*. Pd/NHC-Controlled Regiodivergent Defluorinative Allylation of gem-Difluorocyclopropanes with Allylboronates. ACS Catal. 2022, 12, 6495.

Gao, A. Z.; Chen, S.* Mechanism and Selectivities in Ru-Catalyzed Anti-Markovnikov Formal Hydroalkylation of 1,3-Dienes and Enynes: A Computational Study. J. Org. Chem. 2021, 86, 11895.

• Zhang, C.; Gao, A. Z.; Nie, X.; Ye, C.-X.; Ivlev, S. I.; Chen, S.*; Meggers, E.* Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation. J. Am. Chem. Soc.2021, 143, 13393.

Fall 2024

Principles of Organic Chemistry — CHEM 205

Spring 2025

Principles of Organic Chemistry — CHEM 205
Organic Mechanism and Synthesis — CHEM 325

Notes

Shuming Chen Coauthored Article Published in "Journal of the American Chemical Society"

August 13, 2024

Assistant Professor of Chemistry and Biochemistry Shuming Chen recently published the article “Total Synthesis of (−)-Rauvomine B via a Strain-Promoted Intramolecular Cyclopropanation” in the Journal of the American Chemical Society. Her coauthors include Gabriel Negrao de Morais ’25 as well as collaborators from University of Texas Southwestern Medical Center.

Shuming Chen Coauthored Article Published in "Organic and Biomolecular Chemistry"

May 28, 2024

Assistant Professor of Chemistry and Biochemistry Shuming Chen has recently published an article, "Intermolecular hydrogen bonding behavior of amino acid radical cations," in Organic and Biomolecular Chemistry. Her coauthors are two current Oberlin students, Isabella Moppel ’25 and Barbara Elliott ’26.

Shuming Chen Coauthored Articles Published

January 31, 2024

Assistant Professor of Chemistry and Biochemistry Shuming Chen has recently published two new articles along with Oberlin student coauthors. "Ni-Catalyzed 1,1- and 1,3-Aminoboration of Unactivated Alkenes" has appeared in the Journal of the American Chemical Society with coauthors including Gabriel Negrao de Morais ’25 and collaborators at Indiana University. "C5 methylation confers accessibility, stability and selectivity to picrotoxinin" was published in Nature Communications with coauthors including Anna Crowell ’23 and collaborators from Scripps Research and Corteva Agriscience.

Shuming Chen Recent Coauthored Articles Published

December 6, 2023

Assistant Professor of Chemistry and Biochemistry Shuming Chen has recently published three articles with Oberlin student coauthors. “Chemoselective Quinoline and Isoquinoline Reduction by Energy Transfer Catalysis Enabled Hydrogen Atom Transfer” was published in Angewandte Chemie International Edition with Kyogo Nagashima ’24 and collaborators from Shanghai Jiao Tong University. “Pd/IPrBIDEA-Catalyzed Hydrodefluorination of gem-Difluorocyclopropanes: Regioselective Synthesis of Terminal Fluoroalkenes,” appeared in the Journal of the American Chemical Society with Zachary Cheng ’25 and collaborators from Renmin University of China. Most recently, “Nitrene-Mediated Enantioselective Intramolecular Olefin Oxyamination to Access Chiral γ-Aminomethyl-γ-Lactones,” was published in Angew. Chem. Int. Ed. with Clayton Ritter ’23 and collaborators in Marburg, Germany.

Shuming Chen Recent Papers Published

May 23, 2023

Assistant Professor of Chemistry and Biochemistry Shuming Chen has recently published two papers. "Expedited synthesis of α-amino acids by single-step enantioselective α-amination of carboxylic acids" appeared in Nature Synthesis. Coauthors include Drew Dansby ’24 and collaborators from Marburg, Germany.  "Chemo-, Stereo- and Regioselective Fluoroallylation/Annulation of Hydrazones with gem-Difluorocyclopropanes via Tunable Palladium/NHC Catalysis" was published in Angewandte Chemie. Coauthors on this article include Hieu Nguyen ’25 and collaborators from Renmin University of China.

 

Shuming Chen Awarded Grant from the American Chemical Society

November 16, 2022

Assistant Professor of Chemistry and Biochemistry Shuming Chen has been awarded a $55,000 grant by the American Chemical Society Petroleum Research Fund for her project, "Probing Complex Post-Transition State Bifurcations in Reactions Between Boroles and Unsaturated Hydrocarbons". Professor Chen and her undergraduate research students will use both experimental and computational approaches to study mechanisms in this family of organic reactions.

Shuming Chen publishes Article in ACS Catalysis

September 7, 2022

Assistant Professor of Chemistry and Biochemistry Shuming Chen recently published an article in ACS Catalysis, "Cyclometalated Chiral-at-Ruthenium Catalyst for Enantioselective Ring-Closing C(sp3)–H Carbene Insertion to Access Chiral Flavanones." Co-authors include Peter Choi '23 and collaborators in Marburg, Germany.

Shuming Chen Paper Published in "Nature Communications"

August 16, 2022

Assistant Professor of Chemistry and Biochemistry Shuming Chen recently published a paper in Nature Communications, "Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization." Co-authors on the article include Cassie Davies ’24 and collaborators from UCLA and the University of Arizona.

Shuming Chen Co-Authors Research in 'Nature Chemistry' Journal

April 7, 2022

Assistant Professor of Chemistry and Biochemistry Shuming Chen co-authored a research article in Nature Chemistry with Professor Eric Meggers' research group at the University of Marburg, Germany. This collaborative experimental and computational study reveals that non-covalent interactions, such as π–π stacking, hold the key to stereocontrol (control over three-dimensional shapes of molecules) in a novel synthesis of chiral α-amino acids catalyzed by ruthenium and iron complexes.

Shuming Chen publishes two research articles with Anthony Gao '21

August 20, 2021

Assistant Professor of Chemistry and Biochemistry Shuming Chen and Anthony Gao '21 published two research articles on transition-metal catalysis: "Mechanism and Selectivities in Ru-Catalyzed Anti-Markovnikov Formal Hydroalkylation of 1,3-Dienes and Enynes: A Computational Study" in the Journal of Organic Chemistry; and "Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation" in the Journal of the American Chemical Society. The latter work was published in collaboration with Professor Eric Meggers' research group at the University of Marburg, Germany.
 

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