Jeffrey Cannon

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Research Interests

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.

Courses

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 Spring of odd-numbered years

Publications

Katherine C. Forbes*, Anne Marie Crooke*, Yuri Lee*, Masamu Kawada*, Kian M. Shamskhou*, Rachel A. Zhang*, Jeffrey S. Cannon; "Photoredox-catalyzed Oxidation of Anions for the Atom-Economical Hydro-, Amido-, and DIalkylation of Alkenes," J. Org. Chem. 2022, 87, 3498–3510. doi: 10.1021/acs.joc.1c03055

Donald R. Deardorff, Scott W. Niman*, Mark I. Paulsen*, Anasheh Sookezian*, Meghan E. Whalen*, Christopher J. FInlayson*, Collrane Frivold*, Hilary C. Brown*, Jeffrey S. Cannon; "Development of a Combined Enzyle- and Transition Metal-Catalyzed Strategy for the SYnthesis of Heterocycles: Enentioselective Syntheses of (–)-Coniine, DAB-1, and Nectrisine," ACS Omega 2020, 5, 2005–2014. doi: 10.1021/acsomega.9b03990

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