Mondays 1:30 to 3pm; Thursdays 3:30-5pm; and by appointment
Jeff Cannon teaches Organic Chemistry and does research in organic synthesis and catalysis.
The core of all organic molecules is made up of carbon-carbon bonds. Our group is interested in developing new methods for their construction. To accomplish this, we analyze interesting and complex targets to design creative and highly efficient methods for their synthesis. We are particularly interested in methods that can accomplish this catalytically and stereoselectively. Our studies are augmented by utilizing computational methods to help predict and explain experimental results.
Organic Chemistry I and II (Chem 220 and 221)
Introductory organic chemistry is designed to give students the skills to understand the structure and interactions of covalently-bonded molecules containing carbon. Key topics include structure and intermolecular interactions, reactivity, and synthesis. Special emphasis is placed on developing logical problem-solving skills around multi-step synthesis and electron motion in reaction mechanisms.
Organic Chemistry Labs I and II (Chem 220L and 221L)
Organic chemistry lab teaches the techniques and general reactions of organic chemistry. The first semester focuses on introducing proper techniques for conducting reactions, purifying products, and analyzing the structure and purity of these products. The second semester applies these techniques to the synthesis of several interesting organic molecules.
Physical Organic Chemistry (Chem 360)
Physical organic chemistry is the detailed study of organic reactions and their mechanisms. In this class, students are given the tools to create mechanistic hypotheses for organic processes and design experiments to support or disprove them. Students will be able to utilize frontier molecular orbital theory to make generalizations about reactivity. Students will also be exposed to density functional theory (DFT) as a method for studying the structure and reactivity of organic reactions.
Offered in Fall of even-numbered years
Organic Synthesis (Chem 380)
Organic synthesis is the application of reactions and strategies for the de novo synthesis of complex organic molecules. This class introduces retrosynthetic analysis as a method for approaching complex molecule synthesis. New strategies for synthesis are discussed, with a special emphasis on stereoselective carbon-carbon bond forming reactions.
Offered in Fall of odd-numbered years
Jeffrey S. Cannon, Larry E. Overman; "Discussion Addendum for Preparation of the COP Catalysts: [(S)-COP-OAc]2, [(S)-COP-Cl]2, and (S)-COP-hfacac," Org. Synth. 2018, 95, 500-511. doi: 10.15227/orgsyn.095.0500
Natalie C. Dwulet*, Tina A. Zolfaghari*, Molly L. Brown*, Jeffrey S. Cannon; "Diastereoselective Synthesis of Unnatural Amino Acids by alkylation of α-tert-Butanesulfinamide Auxiliary-Bound Enolates," J. Org. Chem. 2018, 83, 11510-11518. doi: 10.1021/acs.joc.8b01379
Nicholas J. Foy*, Katherine C. Forbes*, Anne Marie Crooke*, Maxwell D. Gruber*, Jeffrey S. Cannon; "Dual Lewis Acid/Photoredox-Catalyzed Addition of Ketyl Radicals to Vinylogous Carbonates in the Synthesis of 2,6-Dioxabicyclo[3.3.0]octan-3-ones," Org. Lett. 2018, 20, 5727-5731. doi: 10.1021/acs.orglett.8b02442
Jeffrey S. Cannon; "A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine," Org. Lett. 2018, 20, 3883-3887, doi: 10.1021/acs.orglett.8b01464
Shao-Xiong Luo, Jeffrey S. Cannon, Buck L. H. Taylor, Keary M. Engle, K. N. Houk, Robert H. Grubbs; "Z-Selective Cross-Metathesis and Homodimerization of 3E-1,3-Dienes: Reaction Optimization, Computational Analysis, and Synthetic Applications," J. Am. Chem. Soc. 2016, 14039-14046, doi: 10.1021/jacs.6b08387
Jeffrey S. Cannon, Larry E. Overman; "Palladium(II)-Catalyzed Enantioselective Reactions Using COP Catalysts," Acc. Chem. Res. 2016, 2220-2231. doi: 10.1021/acs.accounts.6b00398
Jeffrey S. Cannon, Lufeng Zou, Peng Liu, Yu Lan, Daniel J. O'Leary, K. N. Houk, Robert H. Grubbs; "Carboxylate-Assisted C(sp3)-H Activation in Olefin Metathesis-Relevant Ruthenium Complexes." J. Am. Chem. Soc. 2014, 136, 6733-6743. doi: 10.1021/ja5021958
Jeffrey S. Cannon, Robert H. Grubbs; “Alkene Chemoselectivity in Ruthenium-Catalyzed Z‑Selective Olefin Metathesis,” Angew. Chem., Int. Ed. 2013, 52, 9001–9004. doi: 10.1002/anie.201302724
Jeffrey S. Cannon, Angela C. Olson, Larry E. Overman; “Palladium(II)-Catalyzed Enantioselective Synthesis of 2-Vinyl Oxygen Heterocycles,” J. Org. Chem. 2012, 77, 1961–1973. doi: 10.1021/jo202553a
Jeffrey S. Cannon, James H. Frederich, Larry E. Overman; “Palladacyclic Imidazoline-Naphthalene Complexes: Synthesis and Catalytic Performance in Pd(II)-Catalyzed Enantioselective Reactions of Allylic Trichloroacetimidates,” J. Org. Chem. 2012, 77, 1939–1951. doi: 10.1021/jo2025724
Jeffrey S. Cannon, Larry E. Overman; “Is There No End to the Total Syntheses of Strychnine? Lessons to be Learned for Strategy and Tactics in Total Synthesis,” Angew. Chem., Int. Ed. 2012, 51, 4288–4311. doi: 10.1002/anie.201107385
Jeffrey S. Cannon, Stefan F. Kirsch, Larry E. Overman; “Catalytic Asymmetric Synthesis of Chiral Allylic Esters,” J. Am. Chem. Soc. 2010, 132, 15185–15191. doi: 10.1021/ja106685w
Jeffrey S. Cannon, Stefan F. Kirsch, Larry E. Overman, Helen F. Sneddon; “Mechanism of the Cobalt Oxazoline Palladacycle (COP)-Catalyzed Asymmetric Synthesis of Allylic Esters,” J. Am. Chem. Soc. 2010, 132, 15192–15203. doi: 10.1021/ja106688j