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Michael Harmata

Research Emphasis

Synthetic Organic Chemistry, [4+3] Cycloadditions, Synthesis and Chemistry of Benzothiazines, Cyclopentadienone Chemistry, Retro-Nazarov Reaction, Kagan's Ether Chemistry, Trögers Base Chemistry, High Energy Materials,Catalysis and Total Synthesis

Education

  • AB, University of Illinois-Chicago, 1980
  • PhD, University of Illinois-Urbana, 1985

Professional Experience

  • Norman Rabjohn Distinguished Professor of Chemistry, 2000-present
  • Professor, University of Missouri, 1998-2000
  • Associate Professor, University of Missouri, 1992-1998
  • Assistant Professor, University of Missouri, 1986-1992
  • NIH Postdoctoral Fellow, Stanford University, 1985-1986

Honors and Awards

  • 2014
    Fuldner Faculty Fellow, University of Missouri-Columbia
  • Oct 21, 2011
    Sigma-Aldrich Lectureship, University of Nevada-Reno
  • 2011
    Invited Guest Professor, University of Strasbourg
  • 2011
    Japan Society for the Promotion of Science Fellow
  • 2010
    Prose Award-Honorable Mention-for Silver in Organic Chemistry
  • 2010
    Adjunct Professor, International Institute of Nano and Molecular Medicine
  • 2010
    Liebig Professorship, University of Giessen
  • 2008
    Research Fellowship, Alexander von Humboldt Foundation (Reinvitation)
  • 2006
    Big 12 Facutly Fellow, University of Texas-Austin
  • 2000
    Norman Rabjohn Distinguished Professorship, University of Missouri
  • 1998
    Research Fellowship, Alexander von Humboldt Foundation
  • 1997
    Arts and Science Student Government "Blue Chalk" Advising Award
  • 1985
    NIH Postdoctoral Fellowship, Stanford University

Professional Activities

  • Chair, Gordon Research Conference on Organic Reactions and Processes, 2000.
  • Editor: Advances in Cycloaddition, 1997-2001
  • Editor: Strategies and Tactics in Organic Synthesis, 2002-present
  • Member, Chemtracts Organic Chemistry Board, 2002-present
  • Editorial Board, Mini Reviews in Organic Chemistry, 2003-present

  Research

My research program encompasses many areas of organic chemistry with a principal focus on pericyclic reactions of reactive intermediates.  We have also made significant contributions to molecular recognition and supramolecular chemistry in the course of our work on derivatives of Kagan’s ether and Tröger’s base.

In the area of (4+3)-cycloaddition chemistry, we are now especially interested in new mild methods to generate allylic cations. Our newest work is centered on the development of asymmetric processes and the application of methodology we have invented to the synthesis of biologically active natural products, compounds which served as drug leads or important tools for discovering the molecular mechanism by which small molecular produce their effects in living systems.

Our work with Kagan's ether and Tröger's base centers on the development of new chiral templates for applications in catalysis, molecular recognition and supramolecular chemistry. One current goal is developing a series of molecules for a process we call asymmetric charge transfer catalysis.  Another concerns the design and synthesis of new ligands for the actinide elements

We are actively engaged in allenic sulfone and allylic sulfone chemistry.  We have developed methods for the synthesis of value-added, boronated allylic sulfones and have invented a number of new processes that increase the synthetic value of allenic sulfones.

Finally, the construction of new chiral ligands for applications in asymmetric catalysis is one goal of our work involving the cyclic sulfoximines known as benzothiazines. We have also developed methodology that is applicable to the asymmetric total synthesis of a wide variety of natural products, including those of the pseudopterosin class. These compounds have biological activities that include powerful analgesic effects and potent antitubercular activity.

  Recent Representative Publications

“Catalytic Generation of Vinylthionium Ions.  (4+3)-Cycloadditions and Friedel-Crafts Alkylations.”  Michael Topinka, Rama Rao Tata and Michael Harmata.  Organic Letters 2014, 16, 0000.

“A New Synthesis of a’-Hydroxydienones.”  Rama Rao Tata, Carissa S. Hampton, Erich F. Altenhofer, Michael Topinka, Weijiang Ying, Xuefeng Gao and Michael Harmata.  Chemistry A European Journal 2014, 20, 0000.

“Regiodivergent Synthesis of 1- and 2-Arylsulfonyl-1,3-Dienes.”  Carissa S. Hampton and Michael Harmata.  Organic Letters 2014, 16, 1256–1259.

“Synthesis of Functionalized Cyclic Boronates.”  Erich Altenhofer and Michael Harmata.  Organic Letters 2014, 16, 1-4.

“Formation and Ring-Opening of 8-Oxabicyclo[3.2.1]oct-6-en-3-ones from (4+3)-Cycloaddition of Furan and Chlorocyclopentanone Derivatives.” Xuefeng Gao and Michael Harmata.  Tetrahedron 2013, 69, 7675–7682.

“Chemical Synthesis of 1’-Deoxy-1’-Fluorosucrose.”  Weijiang Ying, Vikram Gaddam and Michael Harmata. Organic Letters 2013, 15, 2723–2725.

“Application of the [4+3]-Cycloaddition Reaction to the Synthesis of Natural Products.”  Darin E. Jones and Michael Harmata.  In Methods and Applications of Cycloaddition Reactions in Organic Synthesis; Nishiwaki, N., Ed.; Wiley:  New York, 2014; Chapter 19.

“Further Studies of Benzothiazine Metalation.”  Nathan L. Calkins and Michael Harmata.  Synthesis 2013, 1785-1790.

“Generation and Alkylation of 2-Boryl Allylic Sulfone Anions.”  Erich F. Altenhofer and Michael Harmata.  Chemical Communications  2013, 49, 2365-2367.

“Synthesis Of 6'-Deoxy-6'-Fluorosucrose.” Vikram Gaddam and Michael Harmata.  Carbohydrate Research 2013, 369, 38-41.

“Demethylenation of Tröger’s Bases with Concomitant Hydrazine Formation.”  Xuefeng Gao, Carissa S. Hampton and Michael Harmata.  European Journal of Organic Chemistry 2012, 7053-7056.

“C–N Bond Forming Reactions of Sulfonamides, Sulfoximines, and Other Nitrogen Nucleophiles.”  J. Duan, H. Chen, Xuechuan Hong and Michael Harmata.  Science of Synthesis 2012, 2,255-282.

“Tröger's Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether.”  Kenneth Wärnmark, Victor Snieckus, Victor; Michael Harmata, Josep Artacho, Erhad Asic, Toni Rantanen, Carl-Johan Wallentin, Sami Dawaigher and Karl-Erik Bergquist.  Organic Letters 2012, 14, 4706-4709.

“C-H Activation in S-Alkenyl Sulfoximines:  An Endo 1,5-Hydrogen Migration”  Xuefeng Gao, Vikram Gaddam, Erich Altenhofer, Rama Rao Tata, Zhengxin Cai, Nattawut Yongpruksa, Aswin K. Garimallaprabhakaran and Michael Harmata.  Angewandte Chemie International Edition 2012, 51, 7016-7019.

“Total Synthesis of the Terpenoid Buddledone A: 11-Membered Ring-Closing Metathesis.”  Zhengxin Cai, Nattawut Yongpruksa and Michael Harmata.  Organic Letters 2012, 14, 1661–1663.

“Formation of a Benzothiazine via the Reaction of ortho-halo Sulfoximines with Copper Salts.”  Aswinkumar Garimallaprabhakaran, Xuechuan Hong and Michael Harmata.  ARKIVOC 2012, 119-128.

“Twisted Amide Analogues of Tröger’s Base.”  Josep Artacho, Erhad Ascic, Toni Rantanen, Josefine Karlsson, Carl-Johan Wallentin, Ruiyao Wang, Ola F. Wendt, Michael Harmata, Victor Snieckus and Kenneth Wärnmark.  Chemistry A European Journal 2012, 18, 1038-1042.

Michael Harmata

Rabjohn Distinguished Professor of Chemistry

332 Chemistry
Tel: 573-882-3813
email: HarmataM@missouri.edu

Research

Publications

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