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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

  • 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 17 September 2007)

  • "Diastereoselectivity in an Electrocyclization Reaction of Cyclopentadienones." Michael Harmata, Pinguan Zheng, Peter R. Schreiner and Armando Navarro- Vázquez Tetrahedron Letters 2007, 48, 5919-5922.
  • Benzothiazines in Organic Synthesis. The Preparation of Enantiomerically Pure 4-Substituted Quinolones." Michael Harmata and Xuechuan Hong. Organic Letters 2007, 10, 2701-2704.
  • "Intramolecular Dimerizations of Cyclopentadienones." Michael Harmata and Kanok-on Rayanil. Synthesis 2007, 2370-2378.
  • "Addition of Functionalized Nucleophiles to a Bridgehead Bromoketone." Michael Harmata and Sumrit Wacharasindhu. Synthesis 2007, 2365-2369.
  • "[4+3]-Cycloadditions of Some Allylic Dioxolanes." Michael Harmata, James A. Brackley III and Charles L. Barnes. Tetrahedron Letters 2006, 47, 8151-8155.
  • "Catalytic, Asymmetric [4+3]-Cycloaddition Reactions." Michael Harmata. Advanced Synthesis and Catalysis 2006, 348, 2297-2306.
  • "Sequential Alkylation of Tröger’s Base. An Approach to New Chiral Ligands." Michael Harmata, Kanok-on Rayanil and Charles L. Barnes. Supramolecular Chemistry 2006, 18, 581-586.
  • "Intermolecular [4+2]-Cycloaddtions of a Reactive Cyclopentadienone." Michael Harmata and Maria G. Gomes. European Journal of Organic Chemistry 2006, 2273-2277.
  • "Deantiaromatization as a Driving Force in an Electrocyclic Reaction." Michael Harmata, Pinguan Zheng, Peter R. Schreiner and Armando Navarro-Vázquez, Angewandte Chemie, International Edition 2006, 45, 1966-1971.
  • "Intramolecular 4+3 Cycloadditions. Stereochemical Issues in the Cycloaddition Reactions of Cyclopentenyl Cations. A Synthesis of (+)-Dactylol." Michael Harmata, Paitoon Rashatasakhon and Charles L. Barnes. Canadian Journal of Chemistry, 2006, 84, 145-69.
  • "Benzothiazines in Synthesis. A Synthesis of Pseudopteroxazole." Michael Harmata and Xuechuan Hong. Organic Letters 2005, 8, 3581-3583.
  • "The [4+3]-Cycloaddition/Quasi-Favorskii Process. Synthesis of the Carbocyclic Core of Tricycloclavulone." Michael Harmata and Sumrit Wacharasindhu. Organic Letters 2005, 8, 2563-2565.
  • "Stereospecific Synthesis of Dienones Via a Torquoselective Retro-Nazarov Reaction." Michael Harmata, Dong Reyoul Lee and Charles L. Barnes. Organic Letters 2005, 8, 1881-1883.
  • "Combined Computational and Experimental Studies of the Mechanism and Scope of the Retro-Nazarov Reaction." Michael Harmata, Peter R. Schreiner, Patrick Kirchhoefer and Dong Reyoul Lee. Journal of the American Chemical Society 2004, 126, 10954-10957.
  • "Chiral Molecular Tweezers." Michael Harmata, Accounts of Chemical Research 2004, 37, 862-873.
Michael Harmata

Rabjohn Distinguished Professor of Chemistry

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

Research

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