McNulty, Jim - McMaster University - Department of Chemistry & Chemical Biology

个人简介

Professor Jim McNulty was born on March 9th, 1965 at Bellshill hospital, Glasgow, Scotland. B.Sc. (Hons.) degree at the University of Toronto, Mississauga 1984-1988 (Erindale College). Xerox Research Centre of Canada, 1987 and 1988 NSERC Industrial Scholarships, with Dr. Tony Paine. M.Sc. (1989) and Ph.D. (1993) degrees at University of Toronto, with Professor Ian Still. Postdoctoral Research Associate, University of Geneva, Switzerland,1993-1995, with Professor Charles Jefford. Postdoctoral Research Associate, Arizona State University, Tempe, AZ, 1995-1996, with Professor G.R. Pettit. Assistant/Associate Professor, Department of Chemistry, Brock University, St. Catharines, Ontario, 1996-2003. Cytec Canada, Niagara Falls, Ontario, sabbatical leave. Associate Professor of Chemistry, McMaster University, July 2003-present.

研究领域

Organophosphorous Chemistry The Wittig reaction is one of the premier carbon-carbon bond forming reactions in organic chemistry. Traditionally, the reaction requires a strong base (ex. BuLi, LiHMDS), anhydrous conditions, and the tedious removal of triphenyl phosphine oxide. The McNulty Group has developed a robust methodology for performing Wittig reactions in aqueous conditions with high E selectivity and facile phosphine oxide removal. Current research in the group is focused on expanding the scope of this methodology. Click on the image for more information. Aq Wittig Example Organocatalysis As the name suggests, organocatalysis uses organic molecules to accelerate the rate of a reaction. Amino acids, such as proline, are readily available organocatalysts and can be used in asymmetric syntheses. The McNulty Group has further demonstrated the scope of organocatalysis by developing an organocatalytic, bioorthogonal Wittig reaction. As well, the Group frequently uses organocatalysis as a tool for the development of high value products. Click on the image for an example of an organocatalytic Wittig reaction. Organocatalytic Wittig Homogeneous Metal Catalysis Ligands containing both weakly and strongly coordinating appendages are classified as hemi-labile ligands. Homogeneous catalysis traditionally involves strong ligands, leading to stable complexes. However, hemi-labile ligands when bound to the metal can induce different electronic properties on substrate reactivity through their “on-off” polarization. Hemi-labile ligands play a crucial role in various reactions catalyzed by transition metal complexes. Recently, the McNulty Group prepared a series of stable silver complexes ligated to new 2-phosphinobenzamide hemilabile ligands. The stability and applicability of the well-defined silver complexes toward the first examples of homogeneous azide-alkyne cycloaddition (AAC) reactions was demonstrated. Recent results showed the efficiency of these complexes for hydroamination reactions. In addition to providing mild and novel reactivity, the McNulty Group has explored the pronounced ligand effect for these reactions. Click on the image for more information. Anticancer Drugs Cancer is a growing cause of death and disability worldwide. Recently, the McNulty Group has discovered a series of potent and selective compounds which inhibit aromatase, a clinically validated target for the treatment of ER positive breast cancer. As well, the Group has identified the active pharmacophore of pancratistatin, a natural product known to cause apoptosis in a wide range of tumour lines. Ongoing projects in the Group include the development of improved aromatase inhibitors, and a total synthesis of pancratistatin's pharmacophore. Click on the images for more information.

近期论文

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Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis. J. McNulty*, D. McLeod, P. Das, C. Zepeda-Velázquez, Phosphorus. Sulfur, Silicon & Relat. Elements., in press (2014). Discovery of a new class of cinnamyl-triazole as potent and selective inhibitors of aromatase. J. McNulty*, K. Keskar, A. Holloway, D. Crankshaw, Bioorg. & Med. Chem. Lett., 24, 4586-4589 (2014). Enantioselective Organocatalytic Michael-aldol Sequence to the Anticancer Natural Product (+)-trans-dihydrolycoricidine. J. McNulty*, C. Zepeda-Velazquez, Angew. Chem. Int. Ed. 53, 8450-8454 (2014). See also: Short Synthesis of a Wildflower Alkaloid, Chem. & Eng. News, July 7th, 2014, p. 28-29. See also: Synfacts, 10, 982 (2014). Total Synthesis of the Cyanobacterial Metabolite Nostodione A: Discovery of its Antiparasitic Activity Against Toxoplasma gondii. J. McNulty*, K. Keskar, C. Bordon, R. Yolken, L. Jones-Brando, J. Chem. Soc., Chem. Commun. 50, 8904-8907 (2014). High Yielding Synthesis of Carboranes Under Mild Conditions Using a Homogeneous Silver(I) Catalyst. Direct Evidence of a Bimetallic Intermediate. M. E. El-Zaria, K. Keskar, A. R. Genady, J. A. Ioppolo, J. McNulty, J. F. Valliant*, Angew. Chem. Int. Ed. 53, 5156-5160 (2014). See also: Synfacts, 10, 585 (2014). A robust, well defined homogeneous silver(I) catalyst for mild intramolecular hydroamination of 2-ethynylanilines leading to indoles. J. McNulty*, K. Keskar, Eur. J. Org. Chem. 1622-1629 (2014). Synthesis and anti-toxoplasmosis activity of 4-arylquinoline-2-carboxylate derivatives. J. McNulty*, R. Vemula, C. Bordon, R. Yolken, L. Jones-Brando, Org. Biomolec. Chem., 12, 255-260 (2014). Development of a robust reagent for the two-carbon homologation of aldehydes to (E)-α,β-unsaturated aldehydes in water.J. McNulty*, C. Zepeda, D. McLeod, Green Chemistry, 15, 3146-3149 (2013). A scalable process for the synthesis of (E)-pterostilbene involving aqueous Wittig olefination chemistry. J. McNulty*, D. McLeod, Tetrahedron Lett., 54, 6303-6306 (2013). Investigation of aryl halides as ketone bioisosteres: refinement of potent and selective inhibitors of human cytochrome P450 19A1 (aromatase). J. McNulty*, A. J. Nielsen, C. E Brown, B. R. Difrancesco, N. Vurgun, J. J. Nair; D. Crankshaw, A. Holloway, Bioorg. & Med. Chem. Lett., 23, 6060-6063 (2013). Tandem oxidative radical fragmentation-rearrangement of 2-amino-1,3-benzylidene acetals: A short entry to densely functionalised fully differentiated oxazolidinones. J. McNulty*, J. Calzavara, RSC Advances, 3, 6771-6774 (2013). Phthalide: a direct building-block towards P,O and P,N hemilabile ligands: Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides. J. McNulty*, K. Keskar, Org. Biomolec. Chem., 11, 2404-2407 (2013). Mild chemical and biological synthesis of donor-acceptor flanked reporter stilbenes: Demonstration of a physiological Wittig olefination reaction. J. McNulty*, D. McLeod, Eur. J. Org. Chem. 6127-6131 (2012). Discovery of a robust and efficient homogeneous silver(I) catalyst for the cycloaddition of azides onto terminal alkynes. J. McNulty*, K. Keskar, Eur. J. Org. Chem. 5462-5470 (2012). One-Step Synthesis of Reusable, Polymer-Supported Tri-alkyl Phosphine Ligands. Application in Suzuki-Miyaura and Alkoxycarbonylation Reactions. E. Ullah, J. McNulty*, M. Sliwinski, A. Robertson, Tetrahedron Lett., 53, 3990-3993 (2012). The phosphate-carboxylate mixed-anhydride method: A mild, efficient process for ester and amide bond construction. J. McNulty*, R. Vemula, V. Krishnamoorthy, , A. Robertson, Tetrahedron, 68, 5415-5421 (2012). Highly Chemoselective Mono Suzuki Arylation Reactions on all three Dichlorobenzene isomers and Applications Development. E. Ullah, J. McNulty*, A. Robertson, Eur. J. Org. Chem., 2127-2131 (2012). Synthesizing novel anthraquinone natural product-like compounds to investigate protein-ligand interactions in both an in vitro and in vivo assay. J. McNulty*, N. McKenzie*, D. McLeod, M. McFadden, N. Balachandran, J. Chem. Ed., 89, 743-749 (2012). Discovery of a novel class of aldol-derived 1,2,3-triazoles: potent and selective inhibitors of human cytochrome P450 19A1 (aromatase). J. McNulty*, J. J. Nair, N. Vurgun, B. DiFrancesco, C. Brown, A. Holloway, D. Crankshaw, B. Tsoi, Bioorg. & Med. Chem. Lett., 22, 718-722 (2012). A Novel Synthetic C1 Analog of 7-deoxypancratistatin Induces Apoptosis in p53 Positive and Negative Human Colorectal Cancer Cells by Targeting the Mitochondria: Enhancement of Activity by Tamoxifen. D. Ma, P. Tremblay, K. Mahngar, P. Akbari-Asl, J. Collins, T. Hudlicky, J. McNulty, S. Pandey*, Investig. New Drugs, 30, 1012-1027 (2012).