Department of Chemistry at Illinois State University

Faculty

Hitchcock

Shawn R Hitchcock

Professor, Organic Chemistry

Office Address: 317 Science Laboratory Building
Office Phone: (309)438-7854
Office Hours: MR 12-1 p.m. and by appointment
Email: Contact Shawn Hitchcock (srhitch)
Website: Visit Shawn Hitchcock’s Website
Teaching Schedule:
Course NumberSectionCourse NameTimeRoom NumberCourse Links
CHE220.01Elementary Organic Chemistry MTWR 08:00 - 08:50MLT 0214
CHE233.02Organic Chemistry Laboratory II T R 13:00 - 15:50SLB 0105
CHE290.07Research in Chemistry   
CHE299.07Independent Honor Study in Chemistry   
CHE398.11Professional Practice,Internship in Chemistry   
CHE398.501Professional Practice,Coop in Chemistry   
CHE490.07Research in Chemistry   
CHE498.501Professional Practice,Coop in Chemistry   
Teaching Interests:
My teaching interest in organic chemistry. I have taught courses in sophomore organic chemistry, graduate organic chemistry, and special topics in carbon-carbon bond forming reactions and stereochemistry.

CHE 230: The course is offered as the first in a two-course sequence in a yearlong study of organic chemistry. This course serves to build a strong foundation in the science of organic chemistry for students preparing for careers in the chemical industry, academia, medicine, pharmacy or other health related fields. The class was built about a foundation of lectures, interactive class participation, video presentations and demonstrations that focused on the art and science of organic chemistry.

CHE 232: CHE 232 is offered as the final course in a two-course sequence of organic chemistry and is required for majors. The class builds upon the foundations and introduces new concepts that are directly related to biology and biochemistry. These elements usually bring in the interest of the undergraduates because it is such an interdisciplinary focus.

CHE 380.51: CHE 380.51 is a course that is designed to meet the needs of graduate and undergraduate students. The class is a transitional course that helps undergraduate students and graduate students reinforce the basics that were learned during the sophomore year in college. I have always believed that the establishment of the fundamentals is critical. The examples that are drawn from in class are taken from the immediate chemical literature.

CHE 426: CHE 426 is a class meant to help undergraduate and M.S. graduate students gain of strong understanding of organic chemistry beyond the undergraduate experience. The class covers a number of subjects that are important in contemporary organic synthesis. Many graduate students often tell me that CHE 426 was one of their best classes that they have taken during their graduate career.

Research Interests:
My research interest in the field of molecular asymmetry.

As we move into the 21st century, the needs of society change and evolve. The pharmaceutical industry is changing as well. The emerging challenges in the pharmaceutical field involve many different aspects. One of these aspects is molecular chirality, the capacity of certain molecules to exist as right-handed and left-handed versions. The global sales of such chiral drugs are currently greater than $150 billion per year. Many of these medicinal agents are selectively prepared as either the “right-handed” form or the “left-handed” form as they can exhibit different biological effects.

My research has been focused on developing a variety of methods for the selective preparation of single enantiomer materials. In 2004, funding from the Petroleum Research Fund (administered by the ACS) has allowed me to work with a variety of graduate and undergraduate students in developing a class of chemical reagents capable of inducing the selective formation of chiral materials.

The successes and challenges associated with the oxadiazinones led to emergence of a new research program focused on the use of asymmetric catalysts. The catalysis work led to the establishment of a patent for a method that was developed for the Ephedra alkaloid known as pseudonorephedrine. This work was primarily led by Jonathan Groeper. Before this patent work, pseudonorephedrine was commercially available for nearly $16,800 per gram. This work makes the cost of the material about $20 per gram. Sigma-Alrich also saw the value of his compound and has recently developed its own synthetic procedure to make this material available.

We also developed several new classes of chiral catalysts called oxazolidines, oxadiazines and β-hydroxysalicylhydrazones. These catalysts have shown promise in the application in trials of the asymmetric 1,2-addition of diethylzinc to aromatic and aliphatic aldehydes. This pilot work led to my research group successfully securing a grant from the National Science Foundation in 2007 for $226,050. This grant is being used to increase the diversity of chemical methods that my research group employs in the search for methods of the very selective formation of chiral molecules. Working with a lead graduate student, Raleigh Parrott, an undergraduate student Seshanand Chandrashekar, and high school student Brittany Morgan, we have just published our results of an effective tridentate catalyst in the journal Tetrahedron: Asymmetry.

We have developed several families of ligands that already show much promise in terms of their use in reactions such as the asymmetric allylic alkylation reactions. One of our current targets that we are nearing completion on is the medicinal agent leveteracitam, a clinically effective treatment for epilepsy. In addition to this work, we have developed several families of ligands that already show much promise in terms of their use in reactions such as the asymmetric allylic alkylation reactions.

In conjunction with my research activities, I am constantly developing my mentoring activities with my research students. The activities include weekly meetings where students learn about finding, applying for, and securing positions in the chemical industry.

Students who have worked with me in carrying out studies on chiral materials are employed around the country at companies such as Alcon Laboratories (Texas), Amgen (California), Anderson & Associates (Illinois), DeCode Laboratories (Illinois), GlaxoSmithKline (Pennsylvania). Jonathan Groeper, a 2007 graduate is now employed at Merck Research Laboratories (New Jersey) and Raleigh Parrott II, another 2007 graduate is working with the Federal Bureau of Investigation (Virginia).

Education:
Selected Publications:
C. A. Goodman, C. G. Hamaker, S. R. Hitchcock, "Synthesis and Evaluation of Some Variants of the Nefkens' Reagent," Tetrahedron Letters, 2013, 54 (45), 6012-6014. doi:10.1016/j.tetlet.2013.08.066

C. A. Goodman, J. B. Eagles, L. Rudahindwa, C. G. Hamaker, S. R. Hitchcock, "Synthesis, X-Ray Crystallography, and Reactions of N-Acyl and N-Carbamoyl Succinimides," Synthetic Communications, 2013, 43 (16), 2155-2164. doi:10.1080/00397911.2012.690061

S. Banerjee, B. Smith, S. R. Hitchcock, "A Dimethylzinc/Diphenylphosphinoylimine Approach to the Asymmetric Synthesis of the Calcimimetic Agent NPS R-568," Applied Organometallic Chemistry, 2011, 25 (2), 105-109. doi:10.1002/aoc.1723

J. A. Wolfe, S. R. Hitchcock, "Palladium Catalyzed Asymmetric Sulfonylation Mediated Chiral β-Hydroxy- and β-(o-Diphenylphosphino)benzoyloxy (o-Diphenylphosphino)benzamides," Tetrahedron: Asymmetry, 2010, 21 (21-22), 2690-2695. doi:10.1016/j.tetasy.2010.10.022

M. A. Dean, S. R. Hitchcock, "Synthesis and Application of Oxadiazines as Chiral Ligands for the Enantioselective Addition of Diethylzinc to Aldehydes," Tetrahedron: Asymmetry, 2010, 21 (20), 2471-2478. doi:10.1016/j.tetasy.2010.09.010

G. S. Mahadik, S. R. Hitchcock, "Chiral, Non-racemic Diols, and α-Amino Acid Derived β-Amino Alcohols as Templates for Chiral Catalysts in the Tsuji-Trost Reaction," Tetrahedron: Asymmetry, 2010, 21 (1), 33-38. doi:10.1016/j.tetasy.2009.12.011

S. R. Hitchcock, M. A. Dean, C. J. Kelley, K. L. Edler, G. M. Ferrence, “Synthesis and X-ray Crystal Structures of Chiral, Nonracemic 5,6-Dihydro-4H-1,3,4-oxadiazines,” Journal of Heterocyclic Chemistry, 2010, 47 (4), 982-989. doi:10.1002/jhet.402

S. Banerjee, G. M. Ferrence, S. R. Hitchcock, “Catalytic Asymmetric Addition of Diethylzinc to Aldehydes via Chiral, Non-racemic β-Hydroxy and β-Methoxy Salicylhydrazone Catalysts,” Tetrahedron: Asymmetry, 2010, 21 (7), 837-845. doi:10.1016/j.tetasy.2010.04.021

S. Banerjee, A. J. Camodeca, G. G. Griffin, C. G. Hamaker, S. R. Hitchcock, "Aromatic Motifs in the Design of Ephedra Ligands for Application in the Asymmetric Addition of Diethylzinc to Aldehydes and Diphenylphosphinoylimines," Tetrahedron: Asymmetry, 2010, 21 (5), 549-557. doi:10.1016/j.tetasy.2010.02.026

J. B. Eagles, S. R. Hitchcock, "Synthesis of D-camphor based γ-Amino Acid (1S,3R)-3-Amino-2,2,3-trimethylcyclopentane Carboxylic Acid," Tetrahedron: Asymmetry, 2010, 21 (5), 519-523. doi:10.1016/j.tetasy.2010.03.022

K. L. Edler, S. E. E. Kirk, R. A. Davis, S. R. Hitchcock, G. M. Ferrence, "(5S)-4-(2,2-Dimethylpropyl)-5-isopropyl-1,3,4-oxadiazinan-2-one," Acta Crystallographica, 2010, E66 (12), o3329-o3330. doi:10.1107/S1600536810048798

A. E. Anderson, K. L. Edler, R. W. Parrott II, S. R. Hitchcock, G. M. Ferrence, “(6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl -5-phenyloxazolidin-2-yl]phenol,” Acta Crystallographica, 2010, E66 (4), o902-o903. doi:10.1107/S1600536810009190

I. S. Campbell, K. L. Edler, R. W. Parrott II, S. R. Hitchcock, G. M. Ferrence, “(6S)-2,4-Di-tert-butyl-6-[(4S,5R)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl]phenol,” Acta Crystallographica, 2010, E66 (4), o900-o901. doi:10.1107/S1600536810009074

T. Koyanagi, K. L. Edler, R. W. Parrott II, S. R. Hitchcock, G. M. Ferrence, “(6R)-2-tert-Butyl-6-[(4R,5S)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl]phenol,” Acta Crystallographica, 2010, E66 (4), o898-o899. doi:10.1107/S1600536810009591

G. S. Mahadik, S. A. Knott, L. F. Szczepura, S. J. Peters, J. M. Standard, S. R. Hitchcock, “β-Amino Alcohol Derived β-Hydroxy- and β-(o-Diphenylphosphino)benzoyloxy(o-diphenylphosphino)benzamides: An Ester-Amide Ligand Structural Model for the Palladium-Catalyzed Allylic Alkylation Reaction,” The Journal of Organic Chemistry, 2009, 74 (21), 8164-8173. doi:10.1021/jo9016474

S. Banerjee, J. A. Groeper, J. M. Standard, S. R. Hitchcock, "N-Pyridylmethylephedrine Derivatives in the Catalytic Asymmetric Addition of Diethylzinc to Aldehydes and Diphenylphosphinoylimines," Tetrahedron: Asymmetry, 2009, 20 (18), 2154-2161. doi:10.1016/j.tetasy.2009.08.014