Smith, Andrew - University of St Andrews

个人简介

Andy was born in Middlesbrough and left school to enjoy two years playing football with Aston Villa F.C. before studying for his ‘A’ levels. In 1992 he came up to Jesus College to study Chemistry at the University of Oxford, completing his undergraduate Part II project in 1996 with Professor Steve Davies. Staying at Oxford, he gained a D. Phil under the direction of Professor Steve Davies entitled “Asymmetric Oligomerisation Strategies”. His doctoral research focused upon the development of methodology for asymmetric intra- and intermolecular consecutive conjugate addition reactions, the preparation of polyfunctional and differentially protected β-amino scaffolds and the discovery of a novel oxidative deprotection strategy. Awarded the cross-disciplinary Weston Junior Research Fellowship (by open competition) at New College, University of Oxford in 2000 for post-doctoral studies, a successful research collaboration with Professor Steve Davies was established. During this association he participated in a variety of research topics within the realm of asymmetric synthesis, including the total synthesis of natural products, the development of stereoselective [2,3] sigmatropic rearrangements, the asymmetric synthesis of b-amino acids, ammonium directed oxidative transformations and the use of chiral auxiliaries, resulting in over ninety publications to date. In 2005, he was awarded a Royal Society University Research Fellowship at the School of Chemistry, University of St Andrews and began his independent research career. He was promoted to Reader in 2010, awarded an ERC Starter Grant (Consolidator) in 2011 and promoted to Professor in 2012. He was awarded the RSC Merck Award in 2014 for “outstanding contributions to the creative assembly of enantiopure building blocks by organocatalysis” and is Director of the CRITICAT CDT in Catalysis, a joint initiative by St Andrews, Edinburgh and Heriot-Watt Universities. The main theme of research in the ADS group is the development of new catalysts, novel catalytic reactions and innovative asymmetric synthesis methodologies for chemical synthesis. In all our research projects we aim to discover novel methods and approaches to the assembly of complex functional molecules. Current research is centred upon the use of chiral N-heterocyclic carbenes and isothioureas as asymmetric Lewis base catalysts in a variety of applications in synthesis, as well as asymmetric cascade processes. Alongside these branches of research we utilise physical organic chemistry methods to develop a mechanistic understanding of the processes we study.

研究领域

Synthetic organic chemistry and catalysis has applications that span the breadth of contemporary science, ranging from materials chemistry to chemical biology. Within this remit, our research focuses upon the development of novel (asymmetric) processes using organocatalytic methods, while advancing a mechanistic understanding of these transformations. In all projects we aim to discover novel approaches to the assembly of functional molecules, with progress outlined below and referenced to our publications.

近期论文

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Aryloxide-Facilitated Catalyst Turnover in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis A. Matviitsuk, M. D. Greenhalgh, D.-J. Barrios Antúnez, A. M. Z. Slawin and A. D. Smith Angew. Chem. Int. Ed., 2017, DOI: 10.1002/ange.201706402 N- to C-Sulfonyl Photoisomerisation of Dihydropyridinones: A Synthetic and Mechanistic Study P.-P. Yeh, J. E. Taylor, D. G. Stark, D. S. B. Daniels, C. Fallan, J. C. Walton and A. D. Smith Org. Biomol. Chem., 2017 Tandem Pd and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement S. S. M. Spoehrle, T. H. West, J. E. Taylor, A. M. Z. Slawin, A. D. Smith J. Am. Chem. Soc., 2017, DOI: 10.1021/jacs.7b05619 Aryloxide Promoted Catalyst Turnover in Lewis Base Organocatalysis W. C. Hartley, T. J. C. O’Riordan and A. D. Smith Synthesis, 2017, 49, 3303-3310 Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study T. H. West, D. M. Walden, J. E. Taylor, A. C. Brueckner, R. C. Johnson, P. H.-Y. Cheong, G. C. Lloyd-Jones and A. D. Smith J. Am. Chem. Soc., 2017, DOI: 10.1021/jacs.6b11851 Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides T. H. West, S. S. M. Spoehrle and A. D. Smith Tetrahedron, 2017, DOI: 10.1016/j.tet.2017.01.062 Enantioselective NHC-Catalysed Redox [4+2]-Hetero-Diels-Alder Reactions using α-Aroyloxyaldehydes and Unsaturated Ketoesters J. E. Taylor, A. T. Davies, J. J. Douglas, G. Churchill and A. D. Smith Tetrahedron: Asymmetry, 2017, 28, 355-366 6-exo-trig Michael Addition-Lactonizations for Catalytic Enantioselective Chromenone Synthesis R. M.Neyyappadath, D. B.Cordes, A. M. Z. Slawin and A. D. Smith Chem. Commun., 2017, DOI: 10.1039/c6cc10178j Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines R. W. F. Kerr, M. D. Greenhalgh, A. M. Z. Slawin, P. L. Arnold and A. D. Smith Tetrahedron: Asymmetry, 2017, 28, 125-134 Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl-Alkenyl (sp2 vs sp2) Substituted Secondary Alcohols S. F. Musolino, O. S. Ojo, N. J. Westwood, J. E. Taylor and A. D. Smith Chem. Eur. J., 2016, 22, 18916-18922 Enantioselective Isothiourea Catalysed Michael-Michael-Lactonisation Cascade; Synthesis of δ-Lactones and 1,2,3,4-Substituted Cyclopentanes E. R. T. Robinson, A. B. Frost, P. Elías-Rodríguez and A. D. Smith Synthesis, 2017, 49, 409-423 Exploiting the Imidazolium Effect in Base-free Ammonium Enolate Generation: Synthetic and Mechanistic Studies C. M. Young, D. G. Stark, T. H. West, J. E. Taylor and A. D. Smith Angew. Chem. Int. Ed., 2016, 55, 14394-14399 Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions A. Matviitsuk, J. E. Taylor, D. B. Cordes, A. M. Z. Slawin and A. D. Smith Chem. Eur. J., 2016, 22, 17748-17757 Enantioselective Isothiourea-Catalysed trans-Dihydropyridinone Synthesis using Saccharin-derived Ketimines: Scope and Limitations D. G. Stark, C. M. Young, T. J. C. O'Riordan, A. M. Z. Slawin and A. D. Smith Org. Biomol. Chem., 2016, 14, 8068-8073 Catalytic Enantioselective Synthesis of Pyrrolizine Carboxylates using Isothiourea Catalysis: A Synthetic and Computational Study D. G. Stark, P. Williamson, E. R. Gayner, S. F. Musolino, R. W. F. Kerr, J. E. Taylor, A. M. Z. Slawin, T. J. C. O'Riordan, S. A. MacGregor and A. D. Smith Org. Biomol. Chem., 2016, 14, 8957-8965 Non-Bonding 1,5-S•••O Interactions Govern Chemo- and Enantioselectivity in Isothiourea-Catalyzed Annulations of Benzazoles E. R. T. Robinson, D. M. Walden, C. Fallan, M. D. Greenhalgh, P. H.-Y. Cheong and A. D. Smith Chem. Sci., 2016, 7, 6919-6927 Enantioselective Synthesis of 2,3-Disubstituted trans-2,3-Dihydrobenzofurans Using a Brønsted Base/Thiourea Bifunctional Catalyst D. -J. Barrios Antúnez, M. D. Greenhalgh, C. Fallan, A. M. Z. Slawin and A. D. Smith Org. Biomol. Chem., 2016, 14, 7268-7274 Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans K. Kasten, D. B. Cordes, A. M. Z. Slawin and A. D. Smith Eur. J. Org. Chem., 2016, 21, 3619-3624 Isothiourea-Mediated Organocatalytic Michael Addition–Lactonization on a Surface: Modification of SAMs on Silicon Oxide Substrates R. Chisholm, J. D. Parkin, A. D. Smith and G. Hähner Langmuir, 2016, 32, 3130-3138 A Substrate Mimic Allows High-Throughput Assay of the FabA Protein and Consequently the Identification of a Novel Inhibitor of Pseudomonas aeruginosa FabA L. Moynie, A. G. Hope, K. Finzel, J. Schmidberger, S. M. Leckie, G. Schneider, M. D. Burkhart, A. D. Smith, D. W. Gray and J. H. Naismith J. Mol. Biol., 2016, 428, 108-120