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New reactivity: strain as a design principle

The goal this program is to use the unusual reactivity of strained molecules and use it to solve fundamental problems in synthesis.  To this end, we have developed a number of new reactions and transformations of chiral cyclopropenes, methylenecyclopropanes, and trans-cycloalkenes.  The applications extend into materials science, peptide chemistry, the synthesis of natural products and computationally designed analogs, and pharmaceutical research.
   



Some recent publications in this area

Blackman, M. L.; Royzen, M.; Fox, J. M. "The Tetrazine Ligation: Fast Bioconjugation based on Inverse-electron-demand Diels-Alder Reactivity" JACS ASAP

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Fisher, L. A.; Fox, J. M. "Studies on the Stability of Cycloprop-2-ene Carboxylate Dianions and Reactions with Electrophiles" J. Org. Chem. accepted

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Royzen, M.; Yap, G. P. A.; Fox, J. M. “A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation” J. Am. Chem. Soc. 2008, 130, 3760–3761.

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Pallerla, M. K.; Yap, G. P. A.; Fox, J. M. “Co-complexes Derived from Alkene Insertion to Alkyne-dicobaltpentacarbonyl complexes: Insight into the Regioselectivity of Pauson-Khand Reactions of Cyclopropenes” J. Org. Chem. 73, 6137-6141

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Yan, N.; Liu, X.; Pallerla, M.; Fox, J. M. “ Synthesis of Stable Derivatives of Cycloprop-2-ene Carboxylic Acid” J. Org. Chem. 2008, 73, 4283-4286.

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Yan, N.; Liu, X.; Fox, J. M. “Facially Selective and Regioselective Carbometalation of Cyclopropenes by Aryl Grignard Reagents” J. Org. Chem. 2008, 73, 563-568.

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Zhang, F.; Fox, J. M. “Synthesis of Cyclopropene α-Amino Acids by Enantioselective Desymmetrization” Organic Letters, 2006, 8, 2965-2968.

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Liu, X.; Fox, J. M. “Enantioselective, Facially Selective Carbomagnesation of Cyclopropenes” J. Am. Chem. Soc. 2006, 128, 5600-5601.

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Yang, Z.; Xie, X.; Fox, J. M. “Diastereoselective Synthesis of Methylenecyclopropanes from Chiral Cyclopropene Derivatives” Angew. Chem. Int. Edit. 2006, 45, 3960-3962.

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Pallerla, M. K.; Fox, J. M. “Diastereoselective Intermolecular Pauson Khand Reactions of Chiral Cyclopropenes” Organic Letters, 2005, 7, 3593-3596.

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