Trost, Barry M. - Stanford University - Department of Chemistry

个人简介

Biographical Data Education: Undergraduate - B.A. University of Pennsylvania, 1962 Philadelphia Board of Education Scholarship 1959-62 Graduate - Ph.D. Massachusetts Institute of Technology, 1965 Thesis Advisor: H.O. House Thesis Title: The Structure and Reactivity of Enolate Anions. National Science Foundation Predoctoral Fellow 1963-65 Appointments: Stanford University : Professor of Chemistry, 1987. Job and Gertrud Tamaki Professor in the School of Humanities and Sciences, 1990 Chair, 1996 - 2002 Appointments: University of Wisconsin: Assistant Professor of Chemistry, 1965 Associate Professor of Chemistry, 1968 Professor of Chemistry, 1969 Evan P. and Marion Helfaer Professor of Chemistry, 1976 Chairman, 1980-82 Vilas Research Professor of Chemistry, 1982

研究领域

Our research program revolves around the theme of synthesis. There are two major activities - 1) developing the tools, i.e., the reactions and reagents, and 2) creating the proper network of reactions to make complex targets readily available from simple starting materials. One major activity in designing new reactions and reagents involves the development of "chemists' enzymes" - non-peptidic transition metal based catalysts that can perform chemo-, regio-, diastereo-, and especially enantioselective reactions. In doing so, attention must be paid to the question of atom economy to minimize waste, energy, and consumption of raw materials. Synthetic efficiency raises the question of metal catalyzed cycloadditions to rings other than six membered. A general strategy for a "Diels-Alder" equivalent for formation of five, seven, nine, etc. membered carbo- and heterocyclic rings is evolving. An exciting new direction derives from the molecular gymnastics acetylenes undergo in the presence of transition metals. Cycloisomerization to virtually all types of ring sizes and systems with particularly versatile juxtaposition of functionality become special goals. While palladium catalysts represent a major part of our effort, new opportunities for selectivity complementary to that obtained with palladium complexes appear possible with nickel, chromium, molybdenum, ruthenium, iron, and tungsten complexes and bimetallic complexes composed of two different metals. Of prime concern are 1) exploration of unusual oxidation states of metals for new types of reactivity and 2) asymmetric templates that create enantiomerically pure stereogenic centers. Main group chemistry, especially involving silicon, tin, and sulfur, also offers many opportunities for new reaction design. For example, sulfur-containing substrates may function as either electrophiles or nucleophiles depending upon their chemical environment - a duality that allows them to be dubbed "chemical chameleons." Rational design of novel catalysts for an asymmetric direct aldol condensation is an exciting thrust. From these new synthetic tools evolve new synthetic strategies towards complex natural products. Targets include b-lactam antibiotics, ionophores, steroids and related compounds (e.g., Vitamin D metabolites), alkaloids, nucleosides, carbohydrates, and macrolide, terpenoid, and tetracyclic antitumor and antibiotic agents.

近期论文

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Trost, B. M.; Huang, Z. “Catalytic (3+2) Palladium?Aminoallyl Cycloaddition with Conjugated Dienes” Angew. Chem. Int. Ed. (2019), 58, 6396. Trost, B. M.; Bai, Y.; Bai, W.-J.; Schultz, J. E. “Enantioselective Divergent Synthesis of C19-Oxo Eburnane Alkaloids via Palladium-Catalyzed Asymmetric Allylic Alkylation of an N-Alkyl-?,?-unsaturated Lactam” J. Am. Chem. Soc., (2019), 141, 4811. Trost, B. M.; Gnanamani, E.; Hung, C.-I J.; Kalnmals, C. A. “Synthesis of Chiral, Densely Substituted Pyrrolidones via Phosphine-Catalyzed Cycloisomerization” Org. Lett., (2019), 21, 1890. Trost, B. M.; Nagaraju, A.; Wang, F.; Zuo, Z.; Xu, J.; Hull, K. L. “Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Dihydroquinolinones” Org. Lett., (2019), 21, 1784. Trost, B. M.; Tracy, J. S.; Yusoontorn, T. “Vanadium-Catalyzed Coupling of Allenols with Electrophilic Halide Sources for the Formation of alpha-Halo-alpha’,beta’-unsaturated Ketones” Org. Lett., (2019), 21, 1207. Trost, Barry M.; Tracy, Jacob S. “Vanadium-Catalyzed Synthesis of Geometrically Defined Acyclic Tri- and Tetrasubstituted Olefins from Propargyl Alcohols” ACS Catal., (2019), 9, 1584. Trost, B. M.; Hung, C.-I J.; Gnanamani, E. “Tuning the Reactivity of Ketones through Unsaturation: Construction of Cyclic and Acyclic Quaternary Stereocenters via Zn-ProPhenol Catalyzed Mannich Reactions” ACS Catal., (2019), 9, 1549. Trost, B. M. Gnanamani, E.; Kalnmals, C. A.; Hung, C.-I. J.; Tracy, J. S. “Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol” J. Am. Chem. Soc., (2019), 141, 1489. Trost, B. M.; Schultz, J. E. “Palladium-Catalyzed Asymmetric Allylic Alkylation Strategies for the Synthesis of Acyclic Tetrasubstituted Stereocenters” Synthesis (2019), 51, 1. Trost, B. M.; Kalnmals, C. A.; Tracy, J. S.; Bai W.-J. “Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group” Org. Lett. (2018) 20, 8043. Trost, B. M.; Bai, W.-J.; Stivala, C. E.; Hohn, C.; Poock, C.; Heinrich, M.; Xu, S. Rey, J. “Enantioselective Synthesis of des-Epoxy-Amphidinolide N” J. Am. Chem. Soc. (2018), 140, 49, 17316. Trost, B. M.; Huang, Z.; Murhade, G. M. “Catalytic palladium-oxyallyl cycloaddition” Science (2018), 362, 564. Trost, B. M.; Zell, D.; Hohn, C.; Mata, G.; Maruniak, A. “Enantio? and Diastereoselective Synthesis of Chiral Allenes by Palladium?Catalyzed Asymmetric [3+2] Cycloaddition Reactions” Angew. Chem. Int. Ed. (2018), 57, 12916. Trost, B. M.; Gholami, H. “Propene as an Atom-Economical Linchpin for Concise Total Synthesis of Polyenes: Piericidin A” J. Am. Chem. Soc., (2018), 140, 11623. Trost, B. M.; Mata, G. “Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Trimethylenemethane and Fluorinated Ketones” Angew. Chem. Int. Ed. (2018), 57, 12333. Trost, B. M.; Hung, C.-I.; Scharf, M. J. “Direct Catalytic Asymmetric Vinylogous Additions of alpha,beta- and beta,gamma-Butenolides to Polyfluorinated Alkynyl Ketimines” Angew. Chem. Int. Ed. (2018), 57, 11408. Trost, B. M.; Wang, Y. “A Deprotonation Approach to the Unprecedented Amino-Trimethylenemethane Chemistry: Regio, Diastereo, and Enantioselective Synthesis of Complex Amino Cycles” Angew. Chem. Int. Ed. (2018), 57, 11025. Trost, B. M.; Zhang, Lei; Lam, Tom M. “Synthesis of the Aminocyclitol Core of Jogyamycin via an Enantioselective Pd-Catalyzed Trimethylenemethane (TMM) Cycloaddition” Org. Lett. (2018), 20, 3938. Trost, B. M.; Hung, C.-I; Saget, T.; Gnanamani, E. “Branched aldehydes as linchpins for the enantioselective and stereodivergent synthesis of 1,3-aminoalcohols featuring a quaternary stereocentre” Nature Catal. (2018), 523. Trost, B. M.; Kalnmals, C. A. “Sulfones as Synthetic Linchpins: Transition-Metal-Free sp(3)-sp(2) and sp(2)-sp(2) Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds” Chem.-Eur. J. 2018, 24, 9066. Trost, B. M.; Bai, W.-J.; Hohn, C.; Cregg, J. J. “Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Substituted 1H-Indoles and Tryptophan Derivatives with Vinylcyclopropanes” J. Am. Chem. Soc., (2018), 140, 6710. Trost, B. M.; Tracy, J. S.; Saget, T. “Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters” Chem. Sci. (2018), 9, 2975. Trost, B. M.; Tracy, Jacob S. “Organic Synthesis. Use of Alkynes as a Key to Innovation in Designing Structure for Function” Israel J. Chem. (2018), 2, 18. Trost, B. M.; Gnanamani, E.; Tracy, J. S.; Kalnmals C. A. “Zn-ProPhenol Catalyzed Enantio- and Diastereoselective Direct Vinylogous Mannich Reactions between ?,?- and ?,?-Butenolides and Aldimines” J. Am. Chem. Soc., (2017), 139, 18198. Trost, B. M.; Li, X. “Pd-catalyzed asymmetric allylic alkylations via C-H activation of N-allyl imines with glycinates” Chem. Sci. (2017), 8, 6815. Trost, B. M.; Gnanamani, E.; Hung, C.-I. “Controlling Regioselectivity in the Enantioselective N-Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc-ProPhenol” Angew. Chem. Int. Ed. (2017), 56, 10451. Trost, B.M.; Tracy, J.S. "Carbon-Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols" (2017) Org. Lett., 19, 2630 Trost, B.M.; Kalnmals, C.A. "Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes" (2017) Org. Lett. 19, 2346 Trost, B.M.; Cregg, J.J.; Quach, N. "Isomerization of N-Allylamides to Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides" (2017, J. Am. Chem. Soc., 139, 5139. Trost, B.M.; Chan, W.; Malhotra, S. "Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles" (2017) Chem. Eur. J., 23, 4405.