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 goal is to develop a tandem Diels­-Alder/Pauson­-Khand protocol for the production of tetracyclic compounds using a diene containing a cobalt-complexed alkyne. Another project involves production of cyclic alkynes  via the Nicholas reaction for use in click chemistry applications.

One newer project involves a collaboration with Steve Williams's molecular biology laboratory at Smith. The goal is to identify new molecules to combat lymphatic filariasis, and we have already seen some success with natural and synthetic neurolenin derivatives.

He is also interested in the scholarship of teaching and learning, especially related to teaching organic chemistry in the lecture and the laboratory. He is a practitioner of active learning and readily incorporates technology. He also pioneers innovations like course-based research in organic teaching labs.


Selected Publications

Nickerson, L. A.; Shea, K. M. “First-Semester Organic Chemistry during COVID-19: Prioritizing Group Work, Flexibility, and Student Engagement,” J. Chem. Educ. 2020, 97, 3201-3205.

Barnett, K. L.; Shea, K. M.; *McGeough, C.; *Trotta, K.; Williams, S.; Ly, M.; Aloisio, K. “Semester-Long Course-Based Research Project in Second-Semester Organic Chemistry: Synthesizing Potential Lead Compounds for the Treatment of a Neglected Tropical Disease,” J. Chem. Educ. 2020, 97, 1008-1016.

Shea, K. M. “Student Use of Classroom Response Systems to Promote Active Learning,” In Active Learning in Organic Chemistry: Implementation and Analysis; Houseknecht, J. B., Leontyev, A., Maloney, V. M., Welder, C. O., Eds.; ACS Publications, 2019, Chp 6, 87-97.

Gorin, D. J.; Jamieson, E. R.; Queeney, K. T.; Shea, K. M.; Spray, C. G. R “The “pHunger Games”: Manuscript Review to Assess Graduating Chemistry Majors,” J. Chem. Educ. 2016, 93, 2058-2062.

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.