Washington and Lee University

Chemistry Department

 

 

 Marcia B. France, Ph. D. Chemistry California Institute of Technology

Phone Number: (540) 458 - 8879

E-mail: francem@wlu.edu

Office Number: A413

CV | Courses Taught | Research Interests | Research Students Supervised | Education | Awards | Professional Organizations | Grants | Publications | Patents

Courses Taught:

Research Interests:

The France group is interested in the development of transition metal complexes of chiral Schiff base ligands as catalysts for the asymmetric cyclopropanation of olefins by diazo compounds. The cyclopropane functionality occurs in commercial insecticides as well as many natural products of biological importance and can be converted into other organic functional groups. We have investigated one asymmetric cyclopropanation system in which the active catalyst is prepared in situ by the reaction of a chiral Schiff base ligand with one of several copper(I) precursors. When styrene is introduced to the reaction mixture followed by slow addition of ethyl diazoacetate, moderate enantioselectivities are observed. By modifying the substituents on the ligands, we have been able to achieve enantiomeric excesses greater than 50%, with E/Z ratios typically in the range 1.5-2.0. Even more noteworthy, we have also recently obtained promising results with several other metal precursors that are not commonly used in these types of reactions, including a ruthenium complex that, to our knowledge, has never been previously reported as a cyclopropanation catalyst precursor. This system gives enantiomeric excesses over 80% for the cyclopropanation of styrene. Our current research efforts are concentrated on identifying the active species in the ruthenium system in order to further improve its utility. We are also continuing to vary the substituents on the ligands and to investigate the use of other olefins and diazo compounds in both the copper and the ruthenium systems.

 

Research Students Supervised:

41 at W&L (Laura A. Adams, Divya Ajay, 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, W. Chadwick Ellis, Andrew Griffin, Paulianda Griffith, Veronica Griffith, 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 Kuntz, Yinghao Long, Allyn K. Milojevich, Yo Miura, Shane Newhouser, Laura K. Pekman, Patrick J. Renton, W. Michael Seganish, Emily P. Smith, H. Lesley Smith, Tracy A. Stitt, J. Turner Vosseller, Scott M. Wein, Michael Welsh, Ben Yemini, J. Kenneth Zelenak, John P. Zimmer)
2 at Caltech (David Mai, Susie Kohout)

Education

Awards:

Professional Organizations:

Grants:

 

Publications:

Patents:

Undergraduate researchers are listed in italicized type.

 



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