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

Marcia France

Lee-Jackson House
540.458.8746
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)