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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

  • 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 has typically been divided into the following three areas: (1) 4+3 cycloaddition chemistry, (2) the chemistry of Kagan's ether and Troeger's base and (3) the chemistry of benzothiazines.

In the area of 4+3 cycloaddition chemistry, we continue our focus on intramolecular reactions, but have expanded our investigations to the intermolecular area as well. New developments are centered on the developed 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.

figure 1

Our work with Kagan's ether and Troeger'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.

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 also have developed methodology which 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 which include powerful analgesic effects and potent antitubercular activity.

  Recent Representative Publications

(updated on 18 March 2013)

  • “Generation and alkylation of 2-boryl allylic sulfone anions.” Erich F. Altenhofer and Michael Harmata. Chem. Commun. 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.
  • “Benzothiazines in Organic Synthesis. Synthesis of Fluorescent 7-Amino-2,1-Benzothia- zines.” Nattawut Yongpruksa, Siddharth Pandey, Gary A. Baker and Michael Harmata. Organic and Biomolecular Chemistry 2011, 7979-7982.
  • “Carbon to Carbon Anion Relay Chemistry: Facile Generation of Substituted Allyllithium Species.” Pinguan Zheng, Zhengxin Cai, Aswinkumar Garimallaprabhakaran, Parham Rooshenas, Peter R. Schreiner, and Michael Harmata. European Journal of Organic Chemistry 2011, 5255-5260.
  • “Benzothiazines in Organic Synthesis. An Approach to Floresolide B.” Yugang Chen and Michael Harmata. Tetrahedron Letters 2011, 52, 4069-4071.
  • “Efficient Palladium-Catalyzed N-Arylation of a Sulfoximine with Aryl Chlorides.” Nattawut Yongpruksa, Nathan L. Calkins and Michael Harmata. Chemical Communications 2011, 47, 7665-7667.
  • “Silver-Catalyzed Rearrangement of Propargylic Sulfinates: Synthesis Of Allenic Sulfones.” Michael Harmata, Zhengxin Cai and Chaofeng Huang. Organic Syntheses 2011, 88, 309-316.
  • “Thiol-Activated DNA Damage by α-Bromo-2-cyclopentenone.” Chemical Research in Toxicology. Mostafa I. Fekry, Nathan E. Price, Hong Zang, Chaofeng Huang, Michael Harmata, Paul Brown, J. Scott Daniels, and Kent S. Gates 2011, 24, 217-228.
  • “Boric Acid-Mediated N-Acylation of Sulfoximines.” Aswinkumar Garimallaprabhakaran and Michael Harmata. Synlett 2011, 361-364.
  • Oxidation of 4-Methoxyanilines to 1,4-Benzoquinones using Ceric Ammonium Nitrate (CAN).” Yugang Chen, Weijiang Ying and Michael Harmata. Tetrahedron Letters 2011, 52, 480-482.
  • “Studies Directed Towards the Synthesis of Hamigeran B: A Catalytic Oxidative Cyclization.” Zhengxin Cai and Michael Harmata. Organic Letters 2010, 12, 5668-5670.
  • "Toward the Total Synthesis of Elisapterosin B: An Hg(OTf)2-Promoted Diastereoselective Intramolecular Friedel-Crafts Alkylation." Weijiang Ying, Charles L. Barnes and Michael Harmata. Tetrahedron Letters 2011, 52, 177-180.
  • “The (4+3)-Cycloaddition Reaction: Heteroatom-Substituted Allylic Cations as Dienophiles. Michael Harmata. Chemical Communications 2010, 46, 8904-8922.
  • “The (4+3)-Cycloaddition Reaction: Simple Allylic Cations as Dienophiles. Michael Harmata. Chemical Communications 2010, 46, 8886-8903.
  • “Origin of Stereoselectivity in the (4+3) Cycloadditions of Chiral Alkoxy Siloxyallyl Cations with Furan.” Eliabeth H. Krenske, Kendall N. Houk and Michael Harmata. Organic Letters 2010, 12, 444-447.
Michael Harmata

Rabjohn Distinguished Professor of Chemistry

332 Chemistry
Tel: 573-882-1097
email: HarmataM@missouri.edu

Research

Publications

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