Kevin Shea

Professor of Chemistry

Kevin Shea

Contact & Office Hours

Ford Hall 312

413­-585­-4687

Education

Ph.D., Massachusetts Institute of Technology

B.S., Worcester Polytechnic Institute

Biography

Kevin Shea focuses on organic chemistry. His lab uses organic synthesis to investigate new methods for carbon­-carbon bond formation and to develop syntheses of biologically active molecules. Completed research has focused on the application of tandem Nicholas and Pauson­-Khand reactions for the synthesis of tricyclic heterocycles. Ongoing research involves expanding the use of cobalt­-alkyne complexes in organic synthesis. One project is focused on production of dienes containing cobalt-­alkyne complexes and evaluation of these materials in Diels­-Alder reactions.

His ultimate goal is to develop a tandem Diels­-Alder/Pauson­-Khand protocol for the production of tetracyclic compounds. Another project aims to develop novel cationic Diels-Alder dienophiles stabilized by cobalt­-alkyne complexes. A third project involves production of cyclic alkynes for use in click chemistry applications.

Two newer projects involve collaborations with Adam Hall's neuroscience laboratory and Steve Williams' molecular biology laboratory. The work with the Hall lab is focused on the synthesis and biological evaluation of novel anesthetic compounds, while the investigations with the Williams lab are aimed at identifying new molecules to combat lymphatic filariasis.


Selected Publications

Chowdhury, L.; Croft, C. J.; Goel, S.; Zaman, N.; Tai, A. C.-S.; Walch, E. M.; Smith, K.; Page, A.; Shea, K. M.; Hall, C. D.; Jishkariani,D.; Pillai, G. G.; Hall, A. C. "Differential Potency of 2,6-Dimethylcyclohexanol Isomers for Positive Modulation of GABAA Receptor Currents,” J. Pharm. Exp. Therap. 2016357, 570-579.

Shea, K. M. "Beyond Clickers, Next Generation Classroom Response Systems for Organic Chemistry," J. Chem. Educ. 201693, 971-974.

Shea, K. M.; Gorin, D. J.; Buck, M. E. "Literature-Based Problems for Introductory Organic Chemistry Quizzes and Exams," J. Chem. Educ. 201693, 886-890.

Rudnitsky, A., Ellis, G., DiBartolo, P. M., Shea, K., "Developing a Faculty Learning Community Grounded in the Science of How People Learn: A Year­-Long, Faculty­-Led Teaching and Learning Seminar," To Improve the Academy, 2013, 127­-144.

Thomas, R. M., Shea, K. M., "Synthesis of Di­ and Trisubstituted Azulenes Using a Danheiser Annulation as the Key Step: An Advanced Organic Laboratory Experiment," Journal of Chemical Education, 2013, 90, 110­114.

Olson, J. A., Shea, K. M., "Additions and Corrections to Critical Perspective: Named Reactions Discovered and Developed by Women," Accounts of Chemical Research, 2012, 45, 482­-483.

Olson, J. A., Shea, K. M., "Critical Perspective: Named Reactions Discovered and Developed by Women," Accounts of Chemical Research, 2011, 44, 311­-321.

Shea, K. M., "The Diels­-Alder Reaction," Name Reactions for Carbocyclic Ring Formations; Li, J. J., Ed.; Wiley & Sons, Inc.: Hoboken, NJ, 2010; 275­-308.

Closser, K. D., Quintal, M. M., Shea, K. M., "The Scope and Limitations of Intramolecular Nicholas and Pauson­-Khand Reactions for the Synthesis of Tricyclic Oxygen­- and Nitrogen-Containing Heterocycles," The Journal of Organic Chemistry, 2009, 74, 3680­-3688.

Shea, K. M., "The Nicholas Reaction," Name Reactions for Homologations­-1; Li, J. J., Ed.; Wiley & Sons, Inc.: Hoboken, NJ, 2009; 284­-298.

Shea, K. M., "The Grob Fragmentation," Name Reactions for Homologations­-2; Li, J. J., Ed.; Wiley & Sons, Inc.: Hoboken, NJ, 2009; 452­-463.

Shea, K. M., "Martin's Sulfurane Dehydrating Reagent," Name Reactions for Functional Group Transformations; Li, J. J., Corey, E. J., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2007; 248­-264.

Shea, K. M., "Furans and benzo[b]furans," Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; 2nd edition, Li, J. J., Gribble, G. W., Eds.; Elsevier: Boston, MA, 2007; 303­-344.

Shea, K. M., Closser, K. D., Quintal, M. M., "Nicholas Reactions with Carboxylic Acids for the Synthesis of Macrocyclic Diolides," The Journal of Organic Chemistry, 2005, 70, 9088­-9091.

Quintal, M. M., Closser, K. D., Shea, K. M., "Tandem Intramolecular Nicholas and Pauson-Khand Reactions for the Synthesis of Tricyclic Oxygen­-Containing Heterocycles," Organic Letters, 2004, 6, 4949-4952.

Crombie, A. L., Kane, J. L., Jr., Shea, K. M., Danheiser, R. L., "Ring Expansion­-Annulation Strategy for the Synthesis of Substituted Azulenes and Oligoazulenes. 2. Synthesis of Azulenyl Halides, Sulfonates, and Azulenylmetal Compounds and Their Application in Transition­-Metal-Mediated Coupling Reactions," The Journal of Organic Chemistry, 2004, 69, 8652­-8667.

Shea, K. M., "Feist­Bénary Furan Synthesis," Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; John Wiley & Sons: Hoboken, NJ, 2004; 160­-167.

Shea, K. M. "Paal­Knorr Furan Synthesis," Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; John Wiley & Sons: Hoboken, NJ, 2004; 168­-182.

Kane, J. L., Jr., Shea, K. M., Crombie, A., Danheiser, R. L., "A Ring Expansion­-Annulation Strategy for the Synthesis of Substituted Azulenes. Preparation and Suzuki Coupling Reactions of 1­-Azulenyl Triflates," Organic Letters, 2001, 3, 1081­-1084.

Shea, K. M., Lee, K. L., Danheiser, R. L., "Synthesis and Properties of 9­-Alkyl­- and 9­-Arylcyclopenta[a]phenalenes," Organic Letters, 2000, 2, 2353­-2356.