Research Group
Web Page

Associate Professor, Organic Chemistry

B.S. 1990, Wayne State University
Ph.D. 1995, University of California, Davis
Postdoctoral: 1996-1998, University of Wisconsin, Madison

Email: hitchcock@ilstu.edu
Phone: (309)438-7854
Office: 317 Science Laboratory Building

My research is primarily focused on developing new methods for synthesizing medicinal agents that exist as single isomer drugs. Single isomer drugs come about from molecular handedness.

One method for the control and molecular handedness is the use of compounds called chiral auxiliaries. These are molecules that are capable of transferring their handedness to other molecules. The rational design, synthesis and application of chiral auxiliaries continues to be an important facet of synthetic organic chemistry. The Evans' oxazolidinones are heterocyclic chiral auxiliaries that are stoichiometric reagents but yet offer the opportunity for efficient recycling. These reagents have proven themselves to be quite useful in a number of varied reactions, most notably in the aldol addition reaction. These reactions are central to the theme of synthetic organic chemistry because they form new carbon-carbon bonds in a predictable, asymmetric fashion.

My research group is actively engaged in research and development into a new class of chiral auxiliaries known as 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones. The design of these molecules allows for many variations of the core structure. Through synthetic methods, it is possible to use commercially available ephedrine, pseudoephedrine and norephedrine as enantiomerically enriched starting materials. The syntheses for these compounds are straightforward and very manageable. We have been able to do asymmetric aldol reactions and conjugate additions with these chiral auxiliaries and are now actively pursuing the synthesis of the Pfizer's HIV protease inhibitor, Nelfinavir.

Click on photo for a larger image

SELECTED PUBLICATIONS

D.M. Casper, J.R. Blackburn, C.D. Maroules, T. Brady, J.M. Esken, G.M. Ferrence, J.M. Standard,  "Conformational Studies of N₃-Substituted [1,3,4]-Oxadiazinan-2-ones," J. Org. Chem. 67 (2002) 8871-8876.

D.M. Casper, J.R. Burgeson, J.M. Esken, G.M. Ferrence, S.R. Hitchcock, "Towards the Development of a New Class of Chiral Auxiliaries:  Asymmetric Aldol Reactions of 3,4,5,6-Tetrahydro-1,3,4-2H-oxadiazin-2-ones," Organic Letters, 4 (2002) 3739-3742.

S.R. Hitchcock, G.P. Nora, D.M. Casper, J.D. Wiman, J.T. Bentley, C. Stafford, M.D. Squire, "Synthesis of Novel 1,3,4-Oxadiazinane-2-thiones Derived from Ephedrine, Pseudoephedrine and Norephedrine," Journal of Heterocyclic Chemistry, 39 (2002) 1113-1115.

M.D. Squire, A. Burwell, G.M. Ferrence, S.R. Hitchcock, "Enantiomerically enriched vic-aminoalcohols from D-Camphor," Tetrahedron: Asymmetry, 13 (2002) 1849-1854.

S.R. Hitchcock, D.M. Casper, G.P. Nora, J.R. Blackburn, J.T. Bentley, D.C. Taylor, "Synthesis of N4-Substituted [1,3,4]-oxadiazinan-2-ones Derived from Norephedrine," Journal of Heterocyclic Chemistry, 39 (2002) 823-828.

S.R. Hitchcock, G.P. Nora, D.M. Casper, M.D. Squire, C.D. Maroules, G.M. Ferrence, L.F. Szczepura, and J.M. Standard, "X-Ray Crystallographic and ¹³C Nuclear Magnetic Resonance Studies of 3,4,5,6-tetrahydro-2H-
1,3,4-oxadiazin-2-ones Derived from Ephedrine and Pseudoephedrine," Tetrahedron, 57 (2001) 9789-9798.