 A.B. 1996, Harvard University
Ph.D. 2002, California Institute of Technology
Room: 5317a
Phone: 608-262-2268
Email: tyoon@chem.wisc.edu
Position: Associate Professor
“Radical Cation Diels–Alder Cycloadditions by Visible Light Photocatalysis,” Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 19350–19353. Du, J.; Ruiz Espelt, L.; Yoon, T. P. “Photocatalytic Reductive Cyclizations of Enones: Divergent Reactivity of Photogenerated Radical and Radical Anion Intermediates” Chemical Sci. 2011, 2, 2115–2119. Lu, Z.; Shen, M.; Yoon, T. P. “[3+2] Cycloadditions of Aryl Cyclopropyl Ketones by Visible Light Photocatalysis” J. Am. Chem. Soc. 2011, 133, 1162–1164. Benkovics, T.; Guzei, I.; Yoon, T. P. “Oxaziridine-Mediated Oxyamination of Indoles: An Approach to 3-Aminoindoles and Enantioenriched 3-Aminopyrroloindolines” Angew. Chem. Int. Ed. 2010. 49, 9153–9157. M. A.; Lu, Z.; Yoon, T. P. “[2+2] Cycloadditions by Oxidative Visible Light Photocatalysis” Ischay, J. Am. Chem. Soc. 2010, 132, 8572–8574. Du, J.; Yoon, T. P. "Crossed Intermolecular [2+2] Cycloadditions of Acyclic Enones via Visible Light Photocatalysis" J. Am. Chem. Soc. 2009, 131, 14604-14605. Yoon, T. P.; Ischay, M. A.; Du, J. “Visible Light Photocatalysis as a Greener Approach to Photochemical Synthesis” Nature Chem. 2010, 2, 527–532. Williamson, K. S., Yoon, T. P. “Iron-Catalyzed Aminohydroxylation of Olefins” J. Am. Chem. Soc. 2010, 132, 4570–4571. Partridge, K. M.; Guzei, I. A.; Yoon, T. P. "Carbonyl Imines from Oxaziridines: Generation and Cycloaddition of N-O=C Dipoles" Angew. Chem. Int. Ed. 2010, 49, 930-934. David J. Michaelis, Kevin A. Williamson, and Tehshik P. Yoon, "Oxaziridine-Mediated Enantioselective Aminohydroxylation of Styrenes Catalyzed by Copper(II) Bis(oxazoline) Complexes." Tetrahedron 2009, 65, 5518-5124. (Symposium-In-Print issue in honor of Prof. M. J. Krische). Tehshik P. Yoon, "Can Reaction Mechanisms Be Proven? Commentary." J. Chem. Ed. 2009, 86, 556. Allen, C. P.; Turek, A. K.; Yoon, T. P. "Oxaziridine-Mediated Intramolecular Amination of sp3-Hybridized C-H bonds" J. Am. Chem. Soc. 2009, 131, 12560-12561. Benkovics, T. B.; Du, J.; Yoon, T. P. "Anionic Halocuprate(II) Complexes as Catalysts for the Oxaziridine-Mediated Aminohydroxylation of Olefins." J. Org. Chem. 2009, 74, 5545-5552. Michael A. Ischay, Mary E. Anzovino, Juana Du, and Tehshik P. Yoon, "Efficient Visible Light Photocatalysis of [2+2] Enone Cycloadditions." J. Am. Chem. Soc. 2008, 130, 12886. David J. Michaelis, Michael A. Ischay, and Tehshik P. Yoon, "Activation of N-Sulfonyl Oxaziridines Using Copper(II) Catalysts: Aminohydroxylations of Styrenes and 1,3-Dienes." J. Am. Chem. Soc. 2008, 130, 6610.
Katherine M. Partridge, Mary E. Anzovino, and Tehshik P. Yoon, "Cycloadditions of N-Sulfonyl Nitrones Generated by Lewis Acid-Catalyzed Rearrangement of Oxaziridines." J. Am. Chem. Soc. 2008, 130, 2920.
David J. Michaelis, Christopher J. Shaffer, and Tehshik P. Yoon, "Copper(II)-Catalyzed Aminohydroxylation of Olefins." J. Am. Chem. Soc. 2007, 129, 1866.
| 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.
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.
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.
Last Updated: March 1, 2009
Eli Lilly Grant in Pharmaceutical Chemistry, 2010 Camille Dreyfus Teacher-Scholar Award, 2010 Alfred P. Sloan Research Fellowship, 2009 Amgen Young Investigator's Award, 2009 Thieme Chemistry Journal Award, 2009 University Residence Halls Honored Instructor award, 2008 Beckman Young Investigator Award, 2008 Research Corporation Cottrell Scholar award, 2008 UW-Madison Research-Service Award, 2007 National Science Foundation CAREER Award, 2007 Eli Lilly New Faculty Award, 2006 Herbert Newby McCoy Award for Distinguished Graduate Research, 2002 Associated Students of the California Institute of Technology Teaching Award, 2002 Ruth L. Kirschstein National Research Service Award Research Training Grant (NIH) 2002-2004 National Institutes of Health Postdoctoral Research Fellow, 2002-2004 National Science Foundation Graduate Research Fellowship 1996-1998, 2001 Outstanding Graduate Student Instructor Award, University of California, 2000
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