Davis, Rebecca - University of Manitoba

个人简介

Postdoctoral Researcher, Organic Chemistry Advisor: Prof. Karl Anker J?rgensen Centre for Catalysis, Aarhus University Ph.D., Organic Chemistry Advisor: Prof. Dean J. Tantillo University of California, Davis B.Sc., Chemistry Washington State University

研究领域

Amine Oxidation Methods Imines are a fundamental building block in organic synthesis; however, there are few general and mild protocols for the oxidation of amines to imines. We are currently working on metal-free and Metal-Organo cooperative catalytic methos for oxidizing amines. Metal-Organo Cooperative Catalytic Reaction Development Cooperative catalysis, involving both an organo- and transition metal catalyst, is emerging as a method for accessing new enantioselective reactions that are difficult to achieve with a single catalyst system. The combination of these methods allows us to take advantage of the high selectivity provided by organocatalysis and the wide range of transformations accessible through transition metal catalysis. Counter-ion Influences on Selectivity and Reactivity Recent efforts in the field of organocatalysis have focused on the development of new chiral catalysts. It was during this development that the influence of counter-ions in these reactions became evident. As the field continues to expand, there is a growing need for a better understanding of the origins of this enantioselection, which means that the influence of the counter-ions must be addressed. To explore the issues of counter-ion interactions in asymmetric organocatalysis, we will employ a combination of kinetic and computational studies. As there are currently few methods for studying ion interaction computationally, this work will also include the development of a new computational methodology. The importance of this work is two-fold. First, it will provide a better understanding of the effects of counter-ion interactions in asymmetric organocatalysis, which will allow for the development of new catalysts as well as further improvement to known reactions. Secondly, the methods developed to study the counter-ion interactions could be applied to the many other areas of asymmetric ion-coupling catalysis.

近期论文

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Davis, R. L.; Stiller, J.; Naicker, T.; Jiang, H. J?rgensen, K. A. “Organocatalytic Epoxidations: Reactions, Mechanisms and Applications,” Angew. Chem. Int. Ed. 2014, Accepted. Stiller, J.; Poulsen, P. H.; Cruz, D. C.; Douardo, J.; Davis, R. L.; J?rgensen, K. A. “Organocatalytic [4+2] Addition Reactions via Tetraenamine Intermediates,” Chem. Sci. 2014, DOI: 10.1039/C4SC00081A Davis, R. L.; Jensen, K. L.; Gschwend, B.; J?rgensen, K. A. "On the Mechanism of the Organocatalytic Epoxidation of a,b-Unsaturated Aldehydes," Chem. Eur. J. 2014, 20, 64. Wedler, H. B.; Boys, L.; Davis, R. L.; Flynn, D.; Franz, A. K.; Hamann, C. S.; Harrison, J. G.; Lodewyk, M. W.; Milinkevich, K. A.; Shaw, J. T.; Tantillo, D. J.; Wang, S. C., "Nobody Can See Atoms: Science Camps Highlighting Approaches for Making Chemistry Accessible to Blind and Visually-Impaired Students," J. Chem. Educ. 2014, 91, 188. Davis, R. L.; Lodewyk, M. W.; Siebert, M. R.; Tantillo, D. J. "Complex Consequences: Substituent Effects on Metal-Arylmethylium Interactions,” J. Organomet. Chem. 2013, 748, 68. Rodriguez-Escrich, C.; Davis, R. L.; Jiang, H.; Stiller, J.; Johansen, T. K.; J?rgensen, K. A. “Breaking Symmetry with Symmetry: Bifacial Selectivity in Asymmetric Cycloaddition of Anthracene Derivatives,” Chem. Eur. J. 2013, 19, 2932. Jiang, H.; Rodriguez-Escrich, C.; Johansen, T. K.; Davis, R. L.; J?rgensen, K. A. “Organocatalytic Activation of Polycyclic Aromatics for Asymmetric Diels-Alder Reactions,” Angew. Chem. Int. Ed. 2012, 51, 10271. Halskov, K. S.; Johansen, T. K.; Davis, R. L.; Steurer, M.; J?rgensen, K. A. “Cross-trienamines in Asymmetric Organocatalysis,” J. Am. Chem. Soc. 2012, 134, 12943. Wedler, H. B.; Cohen, S. R.; Davis, R. L.; Harrison, J. G.; Siebert, M. R.; Willenbring, D.; Hamann, C. S.; Shaw, J. T.; Tantillo, D. J. “Applied Computational Chemistry for the Blind and Visually Impaired,” J. Chem. Educ. 2012, 89, 1400. Leverett, C. A.; Purohit, V. C.; Johnson, A. G.; Davis, R. L.; Tantillo, D. J.; Romo, D. “Dyotropic Rearrangements of Fused Tricyclic-β-Lactones: Application to the Synthesis of (?)-Curcumanolide A and (?)-Curcumalactone,” J. Am. Chem. Soc. 2012, 134, 13348. Jensen, K. L.; Weise, C. F.; Dickmeiss, G.; Morana, F.; Davis, R. L.; J?rgensen, K. A. “Accessing Both Diastereoisomers Selectively in an Enantioselective, Intramolecular Michael Reaction Using a Single Chiral Organocatalyst and Formal Total Synthesis of (-)-Epibatidine,” Chem. Eur. J. 2012, 18, 11913. Fraile, A.; Scarpino-Schietroma, D. M.; Albrecht, A.; Davis, R. L.; J?rgensen, K. A. “Asymmetric Synthesis of Hexahydropyrrolo-isoquinolines by an Organocatalytic Three-Component Reaction,” Chem. Eur. J. 2012, 18, 2773. Albrecht, L.; Dickmeiss, G.; Acosta, F. C.; Rodriguez-Escrich, C.; Davis, R. L.; J?rgensen, K. A. “Asymmetric Organocatalytic Formal [2+2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis,” J. Am. Chem. Soc. 2012, 134, 2543. Zou, Y.-Q.; Chen, J.-R.; Liu, X.-P.; Lu, L.-Q.; Davis, R. L.; J?rgensen, K. A.; Xiao, W.-J. “Highly Efficient Aerobic Oxidative Hydroxylation of Arylboronic Acids: Photoredox Catalysis using Visible Light,” Angew. Chem. Int. Ed. 2012, 51, 784. Biggs-Houk, J. E.; Davis, R. L.; Wei, J.; Mercado, B. Q.; Olmsetad, M.; Tantillo, D. J.; Shaw, J. T. “Carbon-Carbon Bond Forming Reactions of a-Thioaryl Carbonyl Compounds for the Synthesis of Complex Heterocyclic Molecules,” J. Org. Chem. 2012, 77, 160.