Hall, Dennis - University of Alberta - Department of Chemistry

个人简介

B.S., Ph.D., Université de Sherbrooke

研究领域

Modern organic synthesis stands as a powerful discipline, defining our ability to create and transform new molecules with tailored properties and functions. To advance, organic synthesis relies on the development of new reaction methods that efficiently enable the construction of compounds with precise structural characteristics. The research interests in my laboratory are focused on the development of new reactions and strategies to access functional molecules with potential uses in biology and medicine. As exemplified with the projects described below, we are interested in addressing a wide variety of fundamental and practical problems. To this end, our main approach is to explore applications of organoboron compounds using both rational design and combinatorial strategies. The design of unnatural biopolymers offers an alternative to the peptide backbone with the goal of creating and improving desirable biological properties. For example, our laboratory has developed methods to assemble large encoded libraries (pools of molecules) of bead-supported oligoamines by split-pool synthesis, a powerful combinatorial strategy to rapidly access thousands of distinct compounds in a minimal number of operations (Figure 1). Polyamines, a class of cationic endogenic biopolymer, play vital roles in several cellular events. Using our synthetic libraries and the concept of multivalent ion-pairing, we target the selective binding of polyanionic biomolecules. Boronic acids are also employed as components of artificial biopolymers for their unique ability to form esters with sugars in water. This key feature is exploited in the design of combinatorial libraries of oligoboronate receptors with the objective of discovering potent and selective ligands for cell-surface oligosaccharides of medicinal relevance. Solid-phase organic synthesis is an invaluable tool in combinatorial chemistry. My group is also involved in developing new resins, linkers, reactions and strategies applicable to the elaboration of small molecule libraries with potential in drug discovery and catalysis. One such example is the development and commercialization of N,N-diethanolaminomethyl polystyrene (DEAM-PS), a useful solid support for the immobilization, solid-phase transformations, and resin-to-resin transfer reactions of boronic acids. The development of efficient methods for stereocontrolled synthesis is crucial to allow access to new types of organic compounds with biological interest. Recently we have invented a multicomponent reaction to construct polysubstituted piperidine derivatives in one operation from simple reactants. This stereoselective [4+2]/allylboration tandem reaction can be used both in diversity-oriented synthesis (Fig. 2a) and in target-oriented synthesis of natural products (Fig. 2b). More recently, our laboratory has reported the first examples of metal-catalyzed allylborations, providing general access to γ-lactones with a stereodefined quaternary carbon center (Fig. 2c). Ongoing work is directed at understanding the nature of metal-promoted activation and at optimizing a catalytic enantioselective process. Students involved in these research projects are exposed to a multidisciplinary environment that provides opportunity to develop expertise in a wide range of contemporary concepts and techniques of organic synthesis and combinatorial chemistry.

近期论文

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J. Ding; D. G. Hall; Concise Synthesis and Antimalarial Activity of All Four Mefloquine Stereoisomers Using a Highly Enantioselective Catalytic Borylative Alkene Isomerization, Angewandte Chemie International Edition 2013, 52, 8069-8073. Y. Kotsuchibashi; R. V. C. Agustin; J.-Y. Lu; D. G. Hall; R. Narain; Temperature, pH, and Glucose Responsive Gels via Simple Mixing of Boroxole- and Glyco-Based Polymers, ACS Macro Letters 2013, 2, 260-264. N. Gernigon; H. Zheng; D. G. Hall; Solid-supported ortho-iodoarylboronic acid catalyst for direct amidation of carboxylic acids, Tetrahedron Letters 2013, 54, 4475-4478. H. Zheng; M. Lejkowski; D. G. Hall; Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels-Alder cycloaddition, Tetrahedron Letters 2013, 54, 91-94. F. Lizzi; G. Veronesi; F. Belluti; C. Bergamini; A. L髉ez-S醤chez; M. Kaiser; R. Brun; R. L. Krauth-Siegel; D. G. Hall; L. Rivas; M. L. Bolognesi; Conjugation of Quinones with Natural Polyamines: Toward an Expanded Antitrypanosomatid Profile. Journal of Medicinal Chemistry 2012, 55, 10490–10500. N. Gernigon; R. M. Al-Zoubi; D. G. Hall; Direct amidation of carboxylic acids catalyzed by ortho-iodo arylboronic acids: catalyst optimization, scope, and preliminary mechanistic study supporting a peculiar halogen acceleration effect. Journal of Organic Chemistry 2012, 77, 8386-8400. J. Ding; J. C. H. Lee; D. G. Hall; Stereoselective Preparation of β-Aryl-β-Boronyl Enoates and Their Copper-Catalyzed Enantioselective Conjugate Reduction, Organic Letters 2012, 14, 4462-4465. D. G. Hall; J. C. H. Lee; J. Ding; Catalytic enantioselective transformations of borylated substrates: Preparation and synthetic applications of chiral alkylboronates, Pure and Applied Chemistry 2012, 84, 2263–2277. H. Zheng; G. Sina; N. Shinji; D. G. Hall; Boronic Acid Catalysis as a Mild and Versatile Strategy for Direct Carbo- and Heterocyclizations of Free Allylic Alcohols, Angewandte Chemie International Edition, 2012, 51, 6187-6190. L. Zilke; D. G. Hall; Synthetic Studies Towards the Core Tricyclic Ring System of Pradimicin A, European Journal of Organic Chemistry 2012, 22, 4153-4163. S. Schumacher; F. Gr黱eberger; M. Katterle; C. Hettrich; D. G. Hall; F.W. Scheller; N. G.-Eichelmann; Molecular imprinting of fructose using a polymerizable benzoboroxole: Effective complexation at pH 7.4, Polymer 2011, 12, 2485-2491. J.W. Tomsho†, A. Pal, D.G. Hall, S. J. Benkovic; Ring Structure and Aromatic Substituent Effects on the pKa of the Benzoxaborole Pharmacophore, ACS Medicinal Chemistry Letters 2012, 3, 48-52. S. Schumacher, M. Katterle, C. Hettrich, B.-R. Paulke, D. G. Hall, F. W. Scheller, N. G.-Eichelmann; Label-free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units, Journal of Molecular Recognition 2011, 6, 953-939. J.C.H. Lee, R. McDonald & D.G. Hall; Enantioselective preparation and chemoselective cross-coupling of 1,1-diboron compounds, Nature Chemistry 2011, 3, 894–899. [Highlighted in Synfacts 2012, 8, 89; Syn Form 2012, 3, A22-A25 ("Syn Story")] J. Ding, D.G. Hall; Preparation of chiral secondary boronic esters via copper-catalyzed enantioselective conjugate reduction of β-boronyl-β-alkyl α,β-unsaturated esters, Tetrahedron 2012, 68, 3428-3434. H. Zheng, M. Lejkowski, D.G. Hall; Mild and selective boronic acid catalyzed 1,3-transposition of allylic alcohols and Meyer–Schuster rearrangement of propargylic alcohols, Chemical Science 2011, 2, 1305-1310. [Highlighted in Synfacts 2011, 779] J.C.H. Lee, D.G. Hall; Gold-catalyzed cycloisomerization reactions of boronated enynes, Tetrahedron Letters 2011, 51(2), 321-324. J.Y. Lu; D.G. Hall; Fragmentation Enables Complexity in the First Total Synthesis of Vinigrol, Angewandte Chemie, International Edition 2010, 49(13), 2286-2288. (Highlight) R. Al-Zoubi, D.G. Hall; Mild Silver(I)-Mediated Regioselective Iodination and Bromination of Arylboronic Acids, Organic Letters 2010, 12(11), 2480-2483. H. Zheng, D.G. Hall; Mild and efficient boronic acid catalysis of Diels-Alder cycloadditions to 2-alkynoic acids, Tetrahedron Letters 2010, 51(27), 3561-3564.