Christopher S. Jeffrey
Organic, Bioorganic, Organometallic Chemistry, and Chemical Ecology
B.S. (2002), Carroll College; Ph.D. (2007), University of Minnesota (Thomas R. Hoye); Postdoctoral Fellow (2007-2010), Princeton University (Erik J. Sorensen).
Office: CB 331
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Christopher S. Jeffrey
Research in the Jeffrey laboratory is focused on addressing important, unmet challenges in target directed synthesis. Areas of research are identified using a synergistic approach where (1) inspiration from structurally and biologically interesting molecular targets drives reaction discovery, and (2) innovation in methodology enables new strategies for target-directed synthesis.
Some preliminary areas of research in our laboratory are focused on the development of new methods/strategies to generate and control electrophilic nitrogen species that will enable the direct functionalization of alkenes and C-H bonds-the two most ubiquitous functional groups in organic molecules. These research interests are focused on the development of: (i) new hetero-cycloaddition reactions, (ii) a concise and general synthesis of a family of biologically active alkaloids, and (iii) new methods of metal-mediated amination.
Jeffrey, C. S.; Anumandla, D.; Carson, C. R. 1,4-Diamination of Cyclic Dienes via a (4 + 3) Cycloaddition of Diaza-allyl Cationic Intermediates. Org. Lett. 2012, ASAP, doi: 10.1021/ol302771z
Jeffrey, C. S.; Barnes, K. L.; Eickhoff, J. A.; Carson, C. R. Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4 + 3] Cycloaddition Reactions for Heterocycle Synthesis. J. Am. Chem. Soc. 2011, 133 7688-7691.
Hoye, T.R.; Jeffrey, C.S.; Nelson, D.P. Dynamic Kinetic Resolution During a Vinylogous Payne Rearrangement: A Concise Synthesis of the Polar Pharmacophoric Subunit of (+)-Scyphostatin. Org. Lett. 2010, 12, 52–55.
Frie, J.L.; Jeffrey, C.S.; Sorensen, E.J. A Hypervalent Iodine-Induced Double Annulation Enables a Concise Synthesis of the Pentacyclic Core Structure of the Cortistatins. Org. Lett. 2009, 11, 5394–5397.
Hoye, T.R.; Jeffrey, C.S.; Shao, F. Mosher Ester Analysis for the Determination of Absolute Configuration of Stereogenic (a.k.a. Chiral) Carbinol Carbons. Nature Protocols 2007, 2, 2451-2458.
Hoye, T.R.; Dvornikovs, V.; Fine, J.M.; Anderson, K.R.; Jeffrey, C.S.; Muddiman, D.C.; Shao, F.; Sorensen, P.W.; Wang, J. The Structure Determination of the Sulfated Steroids PSDS and PADS – New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone. J. Org. Chem. 2007, 72, 7544-7550.
Hoye, T.R.; Jeffrey, C.S. Student Empowerment through ‘Mini-Microscale’ Reactions: The Epoxidation of 1.0 mg of Geraniol. J. Chem. Educ. 2006, 83, 919-920.
Sorensen, P.W.; Fine, J.M.; Dvornikovs, V.; Jeffrey, C.S.; Shao, F.; Wang, J.; Vrieze, L.A.; Anderson, K.R.; Hoye, T.R. Mixture of New Sulfated Steroids Functions as a Migratory Pheromone in the Sea Lamprey. Nature Chem. Biol. 2005, 1, 324-328.
Hoye, T.R.; Jeffrey, C.S.; Tennakoon, M.A.; Wang, J.; Zhao, H. Relay Ring-Closing Metathesis (RRCM): A Strategy for Directing Metal Movement Throughout Olefin Metathesis Sequences. J. Am. Chem. Soc. 2004, 126, 10210-10211.