个人简介

BS, cum laude, Brigham Young University (2005) Ph.D., University of Wisconsin-Madison (2009) NIH Postdoctoral Fellow, Stanford University (2010-2013)

研究领域

Organic Chemistry

A multidisciplinary approach to science can enable advances not only at the interface of two fields, but also within strictly disciplinary research. This capacity derives from an acquired understanding of the scientific approach, methods, and techniques used in other disciplines to solve problems. I intend to establish a research program that employs tools and techniques from other disciplines to solve difficult problems in organic synthesis and catalysis. With the experience and understanding gained through these early investigations, my laboratory will be poised to answer important questions at the interface of chemistry and other fields. Students in my group will have the opportunity to work at the interfaces of inorganic and organic synthesis, polymer science and catalysis, and structural biology and catalysis. Polymer-Incarcerated Transition Metal Catalysts for Kumada-Corriu Cross Coupling Reactions The cross coupling of aryl and alkyl organomagnesium reagents with primary and secondary alkyl halides (Kumada-Corriu coupling) is an important method for generating new carbon-carbon bonds. Iron- and nickel- catalyzed cross couplings with Grignard reagents and alkyl halides have been developed as an efficient method for sp3–sp3 carbon–carbon bond formation. However, low catalyst turnover numbers, poor catalyst selectivity, and a general lack of asymmetric processes have limited the application of this method. A major challenge is preventing catalyst over-reduction and aggregation, which deactivates the catalyst and causes ligand dissociation. Polymers have been shown to stabilize low valent transition metals, prevent oligomerization, and provide air-stable catalyst precursors. One project in my laboratory will explore the potential of polymeric materials to stabilize low valent iron and nickel catalysts and promote greater catalyst lifetime and activity. Incorporation of chiral binding elements into the polymer may also provide a new strategy for asymmetric catalysis within the field of Kumada cross coupling reactions. Electrophilic Catalysis with Heterobimetallic Complexes I am broadly interested in new strategies to tune the reactivity and selectivity of transition metal catalysts. Incorporation of an electron-releasing or electron-withdrawing transition metal “ligand” into a bimetallic complex can greatly influence the reactivity of the active metal center. In this manner, enhanced electrophilic and nucleophilic catalysts can be generated through incorporation of an “inorganic ligand,” while maintaining supporting ligands capable of inducing the appropriate selectivity for the desired reaction. The main goal of this project is to understand and utilize heterobimetallic interactions to generate highly active electrophilic transition metal catalysts for organic synthesis. This project will seek to employ heterobimetallic catalysts for the development of olefin activation and C–H functionalization reactions. α-Helical Peptide Scaffolds as Modular, Tunable, Enzyme-Like Catalysts for Multistep Synthesis The enormous breadth of chemical reactions performed in biological systems can be attributed to nature’s ability to construct highly ordered arrangements of catalytic functional groups, or enzyme active sites. In addition, many organisms have evolved the ability to assemble polyketide synthases (PKSs), or multienzyme complexes that are capable of performing multistep synthesis in a linear fashion. Chemists have tried to mimic nature’s efficiency by constructing multifunctional catalysts or by designing multicomponent reactions or multi-catalyst systems. What is still lacking is a system that mimics nature’s ability to form structurally precise collections of functional groups (active sites) in a modular fashion that enables not only catalysis but also multistep synthesis. This project will investigate the use of short helical peptides to display catalytic functional groups in a stereocontrolled fashion to achieve enzyme-like catalysis. This template approach will provide a new strategy for catalyst design and optimization that takes advantage of substrate preorganization and proximity to improve catalytic activity. The helical scaffold will also make possible the design and construction of multifunctional catalysts capable of performing multistep synthetic processes. Research interests include: Organic synthesis, catalysis, natural product total synthesis, inorganic synthesis, polymer chemistry, biocatalysis

近期论文

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Walker, W. K.; Anderson, D. L.; Michaelis, S. A.; Kay, B. M.; Smith, S. J.; Ess, D. H.; Michaelis, D. J. Origin of Fast Catalysis in Allylic Amination Reactions Catalyzed by Heterobimetallic Pd–Ti Complexes. Submitted. Udumula, V.; Davis, D. L.; Minson, P. S.; Michaelis, D. J. "A Dual Approach to Catalyst Optimization for Nanoparticle-Catalyzed Nitroarene Reductions." Submitted. Walker, W. K.; Anderson, D. L.; Stokes, R. W.; Smith, S. L.; Michaelis, D. J. Allylic Aminations with Hindered Secondary Amine Nucleophiles Catalyzed by Heterobimetallic Ti–Pd Complexes. Org. Lett. 2015, 17, ASAPs. DOI: 10.1021/acs.orglett.5b00058 Williamson, K.S.; Michaelis, D.J.; Yoon, T.P. "Advances in the Chemistry of Oxaziridines," Chem. Rev. 2014, 114, 8016-8036. Trost, B. M.; Michaelis, D. J.; Malhotra, S. “Total Synthesis of (–)-18-epi-peloruside A: An Alkyne Linchpin Strategy.” Org. Lett. 2013, 15, 5274­–5277. Trost, B. M.; Michaelis, D. J.; Truica, M. “Dinuclear Zinc–ProPhenol-Catalyzed Enantioselective α-Hydroxyacetate Aldol Reaction with Activated Ester Equivalents.” Org. Lett. 2013, 15, 4516–4519. Trost, B. M.; Michaelis, D. J.; Charpentier, J.; Xu, J. “Palladium-catalyzed asymmetric allylic alkylation of carboxylic acid derivatives: N-acyloxazolinones as ester enolate equivalents.” Angew. Chem. Int. Ed. 2012, 124, 208–112. Trost, B. M.; Lehr, K.; Michaelis, D. J.; Xu, J.; Buckl, A. K. “Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents.” J. Am. Chem. Soc. 2010, 132, 8915–8917. Michaelis, D. J.; Williamson, K. S.; Yoon, T. P. “Oxaziridine-mediated enantioselective aminohydroxylation of styrenes catalyzed by copper(II) bis(oxazoline) complexes.” Tetrahedron 2009, 65, 5118–5124, invited symposium in print. Michaelis, D. J.; Dineen, T. “Ring-opening of aziridines with o-halophenyllithium reagents: synthesis of 2-substituted chiral indolines.” Tetrahedron Lett. 2009, 50, 1920–1923. Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. “Activation of N-sulfonyl oxaziridines using copper(II) catalysts: aminohydroxylations of styrenes and 1,3-dienes.” J. Am. Chem. Soc. 2008, 130, 6610–6615. Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P. “Copper(II)-catalyzed aminohydroxylation of olefins.” J. Am. Chem. Soc. 2007, 129, 1866–1867. Parent, A. A.; Anderson, T. M.; Michaelis, D. J.; Jiang, G.; Savage, P. B.; Linford, M. R. “Direct ToF-SIMS analysis of organic halides and amines on TLC plates.” Applied Surface Science 2006, 252, 6746–6749. Bronson, R. T.; Michaelis, D. J.; Lamb, R. D.; Husseini, G. A.; Farnsworth, P. B.; Linford, M. R.; Izatt, R. M.; Bradshaw, J. S.; Savage, P. B. “Construction of a surface bound metal ion sensor for Cadmium.” Org. Lett. 2005, 7, 1105–1108.