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Shawn Raynard Hitchcock

Professor - Organic Chemistry
Chemistry
Office
Science Laboratory Building - SLB 317
Office Hours
Mon. 4-5pm, Fri. 10-11am, and by appointment
  • About
  • Education
  • Awards & Honors
  • Research

Biography

Went to Wayne State University for BS in chemistry (1990). Attended UC Davis for PhD (1995). Completed post-doctoral study at UW Madison.

Current Courses

220.001Elementary Organic Chemistry

299.007Independent Honor Study In Chemistry

499.007Independent Research For The Master's Thesis

233.002Organic Chemistry Laboratory II

290.007Research in Chemistry

490.007Research In Chemistry

499.001Independent Research For The Master's Thesis

499.102Independent Research For The Master's Thesis Last Term

498.001Professional Practice: Coop in Chemistry

398.007Professional Practice: Internship In Chemistry

490.003Research In Chemistry

Teaching Interests & Areas

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 fundaments 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 & Areas

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 filed 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 irs own synthetic procedure to make this material available. We also developed several new classes of chiral catalysts called oxazolidines, oxadiazines and beta-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).

Ph D Organic Chemistry

University of California at Davis
Davis, CA

ISU ChemClub travel grant for my graduate student, Cassie Goodman

ISU ChemClub, the student affiliate of the American Chemical Society
2013

Golden Key International Honor Society

Golden Key International Honor Society
2012

2012 Panhellenic Professor Appreciation Dinner

Panhellenic Association
2012

Red Tassel Mortar Board Faculty Appreciation Dinner

Red Tassel Mortar Board
2012

College of Arts and Sciences Outstanding College Researcher

College of Arts and Sciences
2010

Mentorship Award

Red Tassel Mortar Board Faculty Staff Appreciation Dinner
2010

The Student Education Association "P.A.W.s Outstanding Professor"

2010

Book, Chapter

Hitchcock, S., Dore, D., & Wolfe, J. Alkaloid Derived Auxiliaries: Miscellaneous Alkaloids. Carreira E.M. and Yamamoto H. (EDs), Comprehensive Chirality. Elsevier 3 (2012): 284-296.
Hitchcock, S., & Dore, D. Alkaloid-Derived Auxiliaries: Ephedra Alkaloids. In: Carreira E.M. and Yamamoto H. (eds.). Carreira E.M. and Yamamoto H. (EDs), Comprehensive Chirality. Elsevier 3 (2012): 248-283.

Journal Article

Interactive X- ray links: QUHMAJ, QUHLUC | Shawn R. Hitchcock, Melissa A. Dean, Christopher J. Kelley, Kate L. Edler, Gregory 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, 982, DOI: 10.1002/jhet.402 link.
Interactive X-ray link: CUZVUP | 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, 837, DOI: 10.1016/j.tetasy.2010.04.021 link.
Anderson, A., Edler, K., Parrott, R., Hitchcock, S., & Ferrence, G. (6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol.. Acta crystallographica. Section E, Structure reports online 66.Pt 4 (2010): o902-3.
Anderson, A., Edler, K., Parrott II, R., Hitchcock, S., & Ferrence, G. (6S)‐2‐tert‐Butyl‐6‐[(4S,5R)‐3,4‐dimethyl‐5‐phenyl oxazolidin‐2‐yl]phenol. Acta Crystallographica, Section E: Structure Reports Online E66(4) (2010): o902-o903.
Anderson, A., Edler, K., Parrot, R., Hitchcock, S., & Ferrence, G. Title not compatible with Digital Measures: (6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl -5-phenyloxazolidin-2-yl]phenol. Acta Cryst. Section E E66 (2010): o902-o903.

Presentations

A one-pot synthesis of the calcimimetic agent Cinacalcet. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Diphenylphosphinobenzamido-oxadiazinones as chiral ligands for the palladium catalyzed asymmetric reactions. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Efforts directed towards the asymmetric synthesis of the two enantiomeric variants of a key fragment of the multi-drug resistance agent Hapalosin. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Efforts toward the synthesis of Saquinavir using chiral auxiliaries. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Efforts towards the synthesis of arundic acid. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Enantioselective additions of diethylzinc to aldehydes and imines. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Generation II oxadiazinones as chiral auxiliaries: A highly diastereoselective synthesis of a key beta-hydroxycarboxylic acid fragment of Hapalosin. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Oxadiazinones as chiral auxiliaries: Asymmetric synthesis of nelfinavir. ISU Undergraduate Research Symposium. Illinois State University. (2012)
Synthesis of a key intermediate of Tamiflu using the Tsuji-Trost asymmetric alkylation. ISU Undergraduate Research Symposium. Illinois State University. (2012)
The asymmetric Henry reaction. ISU Undergraduate Research Symposium. Illinois State University. (2012)

Grants & Contracts

Summer Faculty Fellowship. Illinois State University. Illinois State University. (2012)