Toste, F. Dean - University of California, Berkeley

个人简介

Dean was born in 1971 in Terceira, Azores, Portugal, but soon moved to Canada. While at the University of Toronto, he majored in Chemistry and Biochemistry and went on to obtain a M.Sc. in Organic Chemistry. He then pursued his Ph.D. with Barry Trost at Stanford and a post-doctoral appointment with Robert Grubbs at Caltech. Dean is currently a Professor of Chemistry at UC Berkeley.

研究领域

Organic, Organometallic Chemistry — Organic and organometallic chemistry are employed in the development of new synthetic methods, enantioselective catalysts and strategies for the synthesis of natural products. Research in my group is primarily aimed toward the development of catalysts and catalytic reactions and methods for organic synthesis. Ultimately, we are interested in using these methods to address problems in the synthesis of complex molecules possessing interesting structural, biological and physical properties. As such, our research program spans the areas of organic synthesis, catalysis, and organometallic chemistry. Two mechanistically distinct applications of complexes with metal-ligand multiple bonds are illustrative of our approach. First, we envision a new approach to catalysis utilizing transition metal-ligand pi-bonds to activate sigma-bonds towards addition reactions. We are also examining metal-ligand and ancillary ligand combinations with the ultimate goal of developing enantioselective versions of these reactions. The concept of employing complexes containing metal-ligand multiple bonds as bifunctional catalysts for sigma-bond activation represents a dramatic shift from the traditional applications of metal-oxo complexes as catalysts for atom transfer (epoxidations, aziridinations and dihydroxylation) and for functional group oxidations. Second, we are developing metal-dioxo complexes as catalysts for three-component cycloadditions in which the oxo ligand is one of the partners. We are applying these cycloaddition reactions to the synthesis of natural products such as kallolide A (anti-inflammatory and cytotoxic properties). A second area of research is the development of new catalysts and synthetic methods for the formation of carbon-carbon and carbon-heteroatom bonds. Of particular interest are addition reactions including additions to olefins and alkynes, alkene-alkene coupling and other atom transfer additions. For example, we are investigating catalytic methods for the addition of water and alcohols to enones as an alternative entry into aldol adducts. Our ultimate goal is to develop enantioselective variants of these reactions and utilize them in the synthesis of natural products such as epoxyquinol (antiangiogenic activity), the eudesmanolides (antitumor) and the amphidinolides (cytotoxic).

近期论文

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"Polymer-Encapsulated Metallic Nanoparticles as a Bridge Between Homogeneous and Heterogeneous Catalysis.", Gross, E.; Toste, F. D.; Somorjai, G. A. Catalysis Letters 2015, 145, 126-138 "A Data-Intensive Approach to Mechanistic Elucidation Applied to Chiral Anion Catalysis.", Neel, A. J.; Milo, A.; Toste, F. D.; Sigman, M. S. Science 2015, 347, 737-743 "Stable Gold(III) Catalysts by Oxidative Addition of a Carbon-Carbon Bond", Wu, C.-Y.; Horibe, T.; Jacobsen, C. B.; Toste, F. D. Nature 2015, 517, 449-454 "A Dual Catalytic Strategy for Carbon-Phosphorus Cross-Coupling via Gold and Photoredox Catalysis", He, Y.; Wu, H.; Toste, F. D. Chem. Sci 2015, 6, 1194-1198 "Engineering Clostridium acetobutylicum for Production of Kerosene and Diesel Blendstock Precursors.", Bormann, S.; Baer, Z. C.; Sreekumar, S.; Kuchenreuther, J. M.; Toste, F. D.; Blanch, H. W.; Clark, D. G. Metab. Eng. 2014, 55, 124-130 "The Effect of Host Structure on the Selectivity and Mechanism of Supramolecular Catalysis of Prins Cyclizations", Hart-Cooper, W. M.; Zhao, C.; Triano, R. M.; Yaghoubi, P.; Ozores, H.L.; Burford, K. N.; Toste, F. D.; Bergman; R. G.; Raymond, K. N. Chem. Sci. 2015, 6, 1383-1393 "Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions", Yang, X.; Tao, W.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826-870 "Enantioselective alpha-Amination Enabled by a BINAM-derived Phase-transfer Catalyst", Nelson, H. M.; Patel, J. S., Shunatona, H. P.; Toste, F. D. Chem. Sci. 2015, 6, 170-173 "Nucleophilic Substitution Catalyzed by a Supramolecular Cavity Proceeds with Retention of Absolute Stereochemistry", Zhao, C.; Toste, F. D.; Raymond, K. N.; Bergman, R. G. J. Am. Chem. Soc. 2014, 136, 14409-14412 "An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols", Zi, W.; Wang, Y.-M.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 12864-12867 "Synthesis of Stable Gold(III) Pincer Complexes with Anionic Heteroatom Donors", Johnson, M. W.; Di Pasquale, A. G.; Bergman, R. G.; Toste, F. D. Organometallics 2014, 33, 4169-4172 "Chemocatalytic Upgrading of Tailored Fermentation Products Toward Biodiesel", Sreekumar, S.; Baer, Z. C.; Gross, E.; Padmanaban, S.; Goulas, K.; Gunbas, G;, Alayoglu, S.; Blanch, H. W.; Clark, D. S.; Toste, F. D. ChemSusChem 2014, 7, 2445-2448 "Gold-Catalyzed Allylation of Aryl Boronic Acids: Accessing Cross-Coupling Reactivity with Gold", Levin, M. D.; Toste, F. D. Angew. Chem. Int. Ed. 2014, 53, 6211-6215 "Photoinitiated Oxidative Addition of CF3I to Gold(I) and Facile Aryl-CF3 Reductive Elimination", Winston, M. S.; Wolf, W. J.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 7777-7782 "In-situ IR and X-ray Micro-spectroscopy with High Spatial Resolution of Multistep Organic Transformation in Flow Micro-reactor Catalyzed by Au Nanoclusters", Gross, E.; Shu, X.; Alayoglu, S.; Bechtel, H. A.; Martin, M. C.; Toste, F. D.; Somorjai, G. A. J. Am. Chem. Soc. 2014, 136, 5225-5228 "Asymmetric Fluorination of a-Branched Ketones Enabled by a Synergistic Combination of Chiral Anion Phase-Transfer Catalysis and Enamine Catalysis using Protected Amino Acids", Yang, X; Phipps, R. J.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5225-5228 "Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion", Shu, X.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844-5847 "Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3-Diazenated Pyrroloindolines", Nelson, H. M.; Reisberg, S. H.; Shunatona, H. P.; Patel, J. S.; Toste, F. D.; Angew. Chem. Int. Ed. 2014, 53, 5600-5603 "Application of Fundamental Organometallic Chemistry to the Development of a Gold-Catalyzed Synthesis of Sulfinate Derivatives", Johnson, M. W.; Bagley, S. W.; Mankad, N. P.; Bergman, R. G.; Mascitti, V.; Toste, F. D.; Angew. Chem. Int. Ed. 2014, 53, 4404-4407 "Gold-Catalyzed Redox Synthesis of Imidazo[1,2a]pyridine using Pyridine N-Oxide and Alkynes", Talbot, E. P. A.; McKenna, J. M.; Toste, F. D.; Adv. Synth. Catal. 2014, 356, 687-691 "Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes", Talbot, E. P. A.; Fernandes, T. A.; McKenna, J. M.; Toste, F. D.; J. Am. Chem. Soc. 2014, 136, 4101-4104