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Washington and Lee University

Washington and Lee University

Marcia France

Associate Dean of the College / John T. Herwick, M.D. Professor of Chemistry

Lee-Jackson House
(540) 458-8746 / (540) 458-8879
francem@wlu.edu

Curriculum Vitae

Current Position:  Associate Dean of the College

John T. Herwick, M.D. Professor of Chemistry, July 2009 - present
Professor of Chemistry, June 2007 - July 2009
Associate Professor of Chemistry, June 2000 - May 2007
Co-Director, W&L-St Andrews Educational Partnership for Students in the Sciences and Preparing for the Health Professions, September 2001 - present
Assistant Professor of Chemistry, July 1994-June 2000

Education

  • 1994 Ph.D., Chemistry, California Institute of Technology Pasadena, CA
    Thesis Advisor: Professor Robert H. Grubbs
    Thesis Title: Olefin Metathesis with Group VIII Transition Metal Complexes: Mechanism, Reactivity, and Catalyst Development

  • 1989 M.S., Chemistry, Yale University New Haven, CT

  • 1988 S.B., Chemistry, Massachusetts Institute of Technology Cambridge, MA

Research

The focus of our current research is on the development of ruthenium catalysts for the hydrogenation of esters and ketones to form alcohols. Traditional methods for these transformations require the use of stoichiometric reagents such as lithium aluminum hydride. These reactions generate large quantities of waste, making them environmentally and economically unattractive for industrial applications. In contrast, an effective catalyst for the addition of hydrogen gas to these compounds would only generate trace amounts of side products, making the reactions much more "green." In addition to concerns over the development of more environmentally friendly reagents, the reduction of ketones has an added consideration in that this reaction involves the formation of a new chiral center. Our research also involves developing new chiral catalysts to control the stereochemistry of such a reaction. Stereochemistry is the study of stereoisomers -- compounds that have the same atomic connectivity but differ in their 3-dimensional orientation in space. Objects that have a non-superimposable mirror image (such as your hands) possess the property of chirality. The configuration of organic molecules has a profound impact on their behavior in chiral environments such as the human body; mirror image molecules are seen as different species and possess different chemical properties. For example, different mirror images of pharmaceutical companies can have very different effects in the body. In most cases, one stereoisomer is active while the other, at best, is just a spectator or, at worst, causes serious complications that compromise the efficacy of the drug.

 


Teaching

Selected Publications

France, M. B.; Tardieu, A.; Gok Pinarli, I.; This, H. "The Effect of Sample Size on the Transfer of Water Soluble Compounds from Onions into Aqueous Solutions"; Manuscript in preparation.

France, M. B.; Tardieu, A.; Pichot, G.; Gok Pinarli, I.; This, H. "The Effect of Temperature on the Transfer of Water Soluble Compounds from Onions into Aqueous Solutions"; Manuscript in preparation.

Henne, J.; France, M. B.; Belkhir, K.; This, H. "Boiling Wine: Is There an Influence of Thermal Power? A Quantitative Proton Nuclear Magnetic Resonance Spectroscopic (q 1H NMR) and Colorimetric Study"; J. Food Sci. Submitted.

Carpenter, I.; Eckelmann, S. C; Kuntz, M. T.; Fuentes, J. A.; France, M.B., Clarke, M. L. "Convenient and Improved Protocols for the Hydrogenation of Esters at Near-Ambient Temperatures Using Ru Catalysts Derived from (P,P), (P,N,N) and (P,N,O) Ligands"; Dalton Trans. 2012, 41, 10136-10140.

Phillips, S. D.; Andersson, K. H. O.; Kann, N.; Kuntz, M. T.; France, M. B.; Wawrzyniak, P.; Clarke, M. L. "Exploring the Role of Phosphorus Substituents on the Enantioselectivity of Ru- Catalysed Ketone Hydrogenation Using Tridentate Phosphine-Diamine Ligands"; Catal. Sci. Technol. 2011, 1, 1336-1339. Selected by editors as a "Hot Article."

Diaz-Valenzuela, M. B.; Phillips, S. D.; France, M. B.; Gunn, M. E.; Clarke, M. L; "Enantioselective Hydrogenation and Transfer Hydrogenation of Bulky Ketones Catalysed by a Ruthenium Complex of a Chiral Tridentate Ligand"; Chem. Eur. J. 2009, 15(5), 1227-1232.
Cited as one of the most significant publications of the month in Synfacts 2009, 4, 396.

Fuentes, J. A.; France, M. B.; Slawin, A. M. Z.; Clarke, M. L. "Iridium Complexes of Chiral Diamines Containing Carbon and Nitrogen Stereocentres: Synthesis, Structure, and Evaluation as Transfer Hydrogenation Catalysts" New J. Chem. 2009, 33(3), 466-470.

Clarke, M. L.; France, M. B. "The Carbonyl Ene Reaction" Tetrahedron 2008, 64(38), 9003-9031.

Clarke, M. L.; Jones, C. E. S.; France, M. B. "The First Organocatalytic Carbonyl-Ene Reaction: Isomerisation-Free C-C Bond Formations Catalysed by H-Bonding Thio-ureas" Beilstein J. Org. Chem. 2007, 3: 24.

Clarke, M. L.; France, M. B.; Knight, F. R.; Frew, J. J. R.; Roff, G. J. "Enantio- and Diastereo-selective Hydrogenation of a Fluorinated Diketone"; Synlett 2007, 11, 1739-1741.

Clarke, M. L.; France, M. B.; Fuentes, J. A. Milton, E. J.; Roff, G. J. "A Convenient Catalyst System for Microwave Accelerated Cross-Coupling of a Range of Aryl Boronic Acids with Aryl Chlorides"; Beilstein J. Org Chem. 2007, 3:18.

Wilmes, G. M.; France, M. B.; Lynch, S. R.; Waymouth, R. M. "Effects of Ligand Substitutions on the Rotation Rate of Indenyl Ligands in bis(2-arylindenyl)zirconocenes by NMR Lineshape Analysis and Relaxation in the Rotating Frame"; Organometallics 2004, 23(10), 2405-2411.

France, M. B.; Milojevich, A. K.; Stitt, T. A.; Kim, A. J. "High Trans Selectivity in the Copper Bis(oxazoline) Catalyzed Asymmetric Cyclopropanation of Olefins by Trimethylsilyl Diazomethane"; Tetrahedron Lett. 2003, 44(52), 9287-9290.

Holland, M. G.; Griffith, V. E.; France, M. B.; Desjardins, S. G. "Kinetics of the Ring-Opening Metathesis Polymerization of a 7-Oxanorbornene Derivative by Grubbs Catalyst"; J. Polym. Sci., Part A: Polym. Chem. 2003, 41(13), 2125-2131.

France, M. B.; Alty, L. T.; Earl, T. M. "Synthesis of a 7-oxanorbornene Derivative: A Two-Step Sequence Preparation for the Organic Laboratory"; J. Chem. Educ. 1999, 76, 659.

France, M. B.; Uffelman, E. S. "Ring-Opening Metathesis Polymerization with a Well-Defined Ruthenium Carbene Complex: An Experiment for the Undergraduate Inorganic or Polymer Laboratory"; J. Chem. Educ., 1999, 76, 661.

Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. "A Series of Well-Defined Metathesis Catalysts - Synthesis and Applications of RuCl2(=CHR')(PR3)2"; Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.

France, M. B.; Feldman, J.; Grubbs, R. H. "An Iridium-based Catalyst System for Metathesis/Isomerization of Acyclic Olefins, including Methyl Oleate"; J. Chem. Soc., Chem. Commun. 1994, 1307.

France, M. B.; Paciello, R. A.; Grubbs, R. H. "Initiation of Ring-Opening Metathesis Polymerization in Protic Media. Extension of [Ru(H2O)6]2+ Catalyzed Polymerization to Less-Strained Cyclic Monomers"; Macromolecules 1993, 26, 4739.

France, M. B.; Grubbs, R. H.; McGrath, D. V.; Paciello, R. A. "Chain Transfer During the Aqueous Ring-Opening Metathesis Polymerization of 7-Oxanorbornene Derivatives"; Macromolecules 1993, 26, 4742.

Grubbs, R. H.; Novak, B. M.; McGrath, D. V.; Benedicto, A.; France, M. B.; Nguyen, S. T. "Ruthenium ROMP Catalysts"; Polymer Preprints 1992, 33(1), 1225.

Jacobsen, E. N.; Marko, I.; France, M. B.; Svendsen, J. S.; Sharpless, K. B. "Kinetic Role of the Alkaloid Ligands in Asymmetric Catalytic Dihydroxylation"; J. Am. Chem. Soc. 1989, 111, 737.

Patents

  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; Singapore Patent 51411. Certificate of correction issued Dec 2008.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; European Patent 1375506, filed August 1, 1996. Certificate of Correction issued February 2008.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; European Patent 0842200. Certificate of Correction issued February 2008.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; Japanese Patent Application 2004-137844. Request for Certificate of Correction paperwork filed November 2007.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; Chinese Patent 96197372.2, filed August 1, 1996. Certificate of Correction issued December 2007.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; Chinese Patent Application 200610101678.4, filed August 1, 1996. Certificate of Correction issued December 2007.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; U. S. Patent 7,102,047, filed October 18, 2004, issued September 5, 2006. Certificate of Correction issued May 2007.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; U. S. Patent 6,806,325, filed December 19, 2002, issued October 19, 2004. Certificate of Correction issued December 2006.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; U. S. Patent 6,515,084, filed December 21, 2000, issued February 4, 2003. Request for Certificate of Correction filed July 2007.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; U. S. Patent 6,111,121, filed January 15, 1998, issued August 29, 2000. Request for Certificate of Correction filed July 2007.
  • Grubbs, R. H,; Schwab, P.; Nguyen, S. T.; France, M. B. "High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes"; U. S. Patent 5,831,108, filed July 31, 1996, issued November 3, 1998. Certificate of Correction issued August 2006.
  • Feldman, J.; France, M. B. "Iridium Catalysts for Metathesis of Acyclic Olefins"; U. S. Patent 5,403,802, 1995.
  • Feldman, J.; France, M. B. "Metathesis of Acyclic Olefins Using an Iridium/Silver Catalyst Composition"; U. S. Patent 5,352,812, 1994.

Research Students Supervised

46 at W&L (Laura A. Adams, Divya Ajay, Alexander Baca, Jeffrey Bonham, James A. Browne, Hans T. Carlson, Rebecca A. Clark, David Cooper, Geoffrey C. Cooper, Elizabeth H. Cox, Laetitia Dalmazio (non-W&L volunteer), T. Markley Earl, Susan C. Eckelmann, W. Chadwick Ellis, Andrew Griffin, Paulianda Griffith, Veronica Griffith, Michael L. Grimaldi, Daniel G. Gurnon, Amanda Haines, Wesley A. Hoke, Marium G. Holland, H. Brooks Hooper, Eric D. Huttenbach, G-Yoon Jamie Im, Nicole Johnson, Angela J. Kim, Michael T. Kuntz, Yinghao Long, Allyn K. Milojevich, Yo Miura, Shane Newhouser, Claire Oliver, Laura K. Pekman, Patrick J. Renton, W. Michael Seganish, Emily P. Smith, H. Lesley Smith, Tracy A. Stitt, Robert G. Vestal, J. Turner Vosseller, Scott M. Wein, Michael A. Welsh, Ben Yemini, J. Kenneth Zelenak, John P. Zimmer)
3 at INRA/AgroParisTech (Joris Autran, Guillaume Pichot, Manon Dassy)
2 at St Andrews (Mary E. Gunn, Fergus R. Knight (M. Chem.))
2 at Caltech (David Mai, Susie Kohout)

Professional Organizations

  • 2012 National Association of Fellowship Advisors
  • 1995 Council on Undergraduate Research
  • 1995 Virginia Academy of Science
  • 1988 Phi Beta Kappa
  • 1985 Phi Lambda Upsilon, Honorary Chemical Society
  • 1984 American Chemical Society

Grants and Awards

Grants

  • Engineering and Physical Sciences Research Council (EPSRC) grant; "Highly Reactive Catalysts for the Hydrogenation of Poorly Reactive Substrates," June 2009-August 2010, £21388 (with Matthew Clarke, P.I.).
  • Associated Colleges of the South Andrew W. Mellon Faculty Renewal Program, Professional Development Grant; "Research at the University of St Andrews: Preparation of Chiral Ligands for Asymmetric Catalysis," January 2009-December 2009, $5000.
  • American Chemical Society Petroleum Research Fund - Undergraduate Faculty Sabbatical Grant; "Synthesis of Novel Nitrogen Ligands for Asymmetric Catalysis," July 2005-July 2006, $50,000.
  • Jeffress Memorial Trust Research Grant; "Chiral Schiff Base Complexes as Catalysts for Asymmetric Cyclopropanation," July 1998 - 1999, $19,200; Renewal Grant, January 2004-December 2004, $10,000; Renewal Grant, January 2005-December 2005, $10,000.
  • C.B. Fleet Company, Inc. "Kinetics Studies of the Hydrolysis of Bisocodyl," January 1, 2004 - December 31, 2004, $41,000 (with Steven G. Desjardins).
  • National Science Foundation Major Research Instrumentation grant; "Multinuclear Gradient Inverse Probe, Amplifier, and Overnight Low Temperature Dewar for High-Field NMR Spectroscopy in the Chemistry Department at Washington and Lee University," August 2003- August 2006, $70,830 (with Erich S. Uffelman (project director), Steven G. Desjardins, and Lisa T. Alty).
  • National Science Foundation Research Opportunity Award to support sabbatical leave at Stanford University, August 2000 - August 2001, $18,000 (with Robert M. Waymouth).
  • Japan Society for the Promotion of Science Postdoctoral Fellowship for American Researchers; "Asymmetric Organic Reactions in Chiral Ionic Liquids," awarded January 2000, but declined.
  • Research Corporation Cottrell College Science Award; "Novel Chiral C3 Symmetric Tripodal Isocyanide Ligands," June, 1997 - June, 1999, $30,330.
  • American Chemical Society Petroleum Research Fund; "Chiral Schiff-Base Complexes as Catalysts for Asymmetric Cyclopropanation," September, 1996-September, 1998, $20,000.
  • National Science Foundation Instrumentation and Laboratory Improvement grant; "High-Field Multinuclear NMR In Undergraduate Education at Washington and Lee University," 1996-1998, $99,500 (with Erich S. Uffelman, Lisa T. Alty, and Steven G. Desjardins).

Awards

  • 2009 John T. Herwick, M.D. Professorship in Chemistry
  • 1999 Faculty Travel Award to attend the 1999 National Organic Symposium
  • 1993 Associated Students of the California Institute of Technology Teaching Award
  • 1991 Dow Travel Fellowship
  • 1988 - 1991 National Science Foundation Predoctoral Fellowship
  • 1988 Association of M.I.T. Alumnae Award for the Woman Who Has Shown the Highest Level of Scholastic Achievement in Her Graduating Class
  • 1988 Alpha Chi Sigma Award
  • 1988 American Institute of Chemists Award
  • 1988 Society for Applied Spectroscopy Student Award