Tehshik P. Yoon

Email address: tyoon@chem.wisc.edu

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Yoon Group
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A.B. 1996, Harvard University
Ph.D. 2002, California Institute of Technology

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Research Description

Research Interests
The central theme of research in the Yoon group is the development of new catalytic methods for organic synthesis.  We are most interested in reactions with the following features:

  1. Synthetic utility
    The most important consideration we use in choosing new research problems is the potential to improve upon current state-of-the-art approaches to constructing complex molecular structures.
  2. Mechanistic novelty
    The reactions that capture our attention tend to possess unusual mechanistic features or involve novel modes of catalysis.
  3. Stereoselectivity
    A particular focus of our lab is the development of enantioselective catalysts that can efficiently control the stereochemistry of newly formed bonds.
  4. Sustainability
    We are interested in minimizing the environmental impact and maximizing the long-term sustainability of methods developed in our labs.  

Visible Light Photocatalysis in Organic Synthesis
Sunlight is a safe, inexpensive, and endlessly renewable reagent.  Most organic compounds, however, absorb light only at short wavelengths of ultraviolet light that are relatively poorly emitted in the solar spectrum.  Conventional high-pressure UV photochemical reactions are thus rarely utilized on industrial scales, as they are energy-intensive, hard to scale, and relatively expensive.  We are developing strategies to use transition metal photocatalysts in interesting new photochemical reactions that use visible wavelengths of light.  By enabling the use of direct sunlight in synthetically useful reactions, we hope to pioneer a new, environmentally responsible approach to synthetic organic photochemistry.

Sunlight-promoted reaction

New Reactions of Oxaziridines
A fundamental challenge in synthetic organic chemistry is the ability to add of oxygen- and nitrogen-containing functional groups to otherwise unfunctionalized hydrocarbon feedstocks (alkanes, alkenes, arenes) in a regioselective and stereoselective fashion.  We are investigating the ability of three-membered heterocycles called oxaziridines to perform a wide variety of such oxidative functionalization reactions.  We have developed methods to synthesize a range of structures, including 1,2-aminoalcohols, 1,3-aminoalcohols, isoxazolidines, piperidines, pyrrolidines, tetrahydroisoquinolines, and other structures that are commonly found in biologically active natural products and pharmaceutical agents.

Figure 1

Total Synthesis of Natural Products

The long-term goal of research in our group is the development of new methods for organic synthesis that can find broad applicability in the synthesis of complex molecular structures. The total synthesis of biologically active and architecturally interesting natural products represents the ultimate demonstration of the utility of new reactions and consequently constitutes a vital aspect of our research program. In addition, the challenges encountered in the course of a long multistep synthesis help to inform our approach to new reaction development.

Figure 2

Awards and Honors

WARF Romnes Faculty Fellowship, University of Wisconsin-Madison 2015
Friedrich Wilhelm Bessel Research Award, Alexander von Humboldt Foundation 2014
UW-Madison Chancellor's Distinguished Teaching Award 2013
Fellow, American Association for the Advancement of Science 2013
Camille and Henry Dreyfus Teacher-Scholar Award 2010