Smith, Martin D. - University of Oxford

个人简介

Martin Smith is Professor of Organic Chemistry at the University of Oxford, and the Old Members' Helen Martin Fellow at University College, Oxford. He is also co-director of the CDT in Synthesis for Biology & Medicine. He came up to the University of Oxford from Middlesbrough for his undergraduate studies, then worked with Professor George W. J. Fleet on the chemistry of carbohydrate amino acids, gaining his DPhil in 1999/2000. He then moved to Pembroke College, University of Cambridge as the Drapers Company Research Fellow, to work with Professor Steven V. Ley CBE FRS. In 2003 he began his tenure as a Royal Society University Research Fellow in the Department of Chemistry, University of Cambridge. The group moved to the University of Oxford in October 2008.

研究领域

ENANTIOSELECTIVE CATALYSIS A focus of our current work is the development of catalytic enantioselective methods for the synthesis of complex molecules. We have focused in recent years on the application of chiral counter-ions to control absolute stereochemistry. Our initial work on an approach to enantioselective electrocyclization led to a method for the synthesis of indolines, that provided insight into the mechanism of phase transfer catalysis. We have extended this approach to the synthesis of pyrroloindolines and indolenines, and demonstrated that enantioselective 5-endo-trig Michael addition reactions are not always precluded by geometric constraints (as embodied by the Baldwin rules). TOTAL SYNTHESIS OF NATURAL PRODUCTS We are also engaged in the total synthesis of complex natural products using cascade sequences to shorten or accelerate synthetic sequences. We have completed the synthesis of (-)-Gephyrotoxin via a reductive intramolecular enamine-Michael cascade that delivers the natural product in nine steps and allows confirmation of its absolute configuration. NON-COVALENT INTERACTIONS IN CATALYSIS AND STRUCTURE We have built structures stabilized by hydrogen bonds such as helices, sheets and turns, and have used a designed β-turn construct to generate efficient hydrogen bonding catalysts that provide very high levels of enantioselectivity at low loadings.

近期论文

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Control of Stereogenic Oxygen in a Helically Chiral Oxonium Ion Owen Smith, Mihai V. Popescu, Madeleine J. Hindson, Robert Paton, Jonathan W. Burton & Martin D. Smith.Nature 2023, 615, 430-435. Harnessing Triaryloxonium Ions for Aryne generation Owen Smith, Madeleine J. Hindson, Viorel Tataru, A. Sreenithya, Robert S. Paton, Jonathan W. Burton & Martin D. Smith. ChemRxiv, DOI: 10.26434/chemrxiv-2023-5wwqd Counterion-Mediated Enantioconvergent Synthesis of Axially Chiral Medium Rings Ji-Yuan Du, Tudor Balan, Tim D. W. Claridge & Martin D. Smith.J. Am. Chem. Soc. 2022, 144, 14790-14797. Catalytic Enantioselective 6𝝿 Photocyclization of Acrylanilides Benjamin A. Jones, Pearse Solon, Mihai V. Popescu, Ji-Yuan Du, Robert Paton & Martin D. Smith.J. Am. Chem. Soc. https://doi.org/10.1021/jacs.2c09267 ChemRxiv, DOI: 10.26434/chemrxiv-2022-dnzbk Enantioselective Synthesis of Atropisomeric Indoles via an Iron Catalysed Cxidative Cross Coupling Richard R. Surgenor, Xiangqian Liu, Morgan J. H. Keenlyside, William Myers & Martin D. Smith.Nature Chem. DOI: https://doi.org/10.1038/s41557-022-01095-9 ChemRxiv, DOI: 10.26434/chemrxiv-2021-zprv7-v2 Visible Light Mediated Heterocycle Functionalization via Geometrically Interrupted [2+2] Cycloaddition Mihai Popescu, Aroonroj Mekereeya, Juan V. Alegre-Requena, Robert S. Paton & Martin D. Smith.Angew. Chem. Int. Ed. 2020, 59, 23020. A Halogen-Bonding Foldamer Molecular Film for Selective Reagentless Anion Sensing in Water Robert Hein, Arseni Borrisov, Martin D. Smith, Paul D. Beer & Jason J. Davis.Chem. Commun. 2019, 55, 4849. Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion Benjamin A. Jones, Tudor Balan, John D. Jolliffe, Craig D. Campbell & Martin D. Smith.Angew. Chem. Int. Ed. 2019, 58, 4596. Anion Recognition in Water by Charge-Neutral Halogen and Chalcogen Bonding Foldamer Receptors Arseni Borrisov, Igor Marques, Jason Y. C. Lim, Vítor Félix, Martin D. Smith & Paul D. Beer.J. Am. Chem. Soc. 2019, 141, 4119. Hydrogen Bond Enabled Dynamic Kinetic Resolution of Axially Chiral Amides Mediated by a Chiral Counterion Alison J. Fugard, Antti S. K. Lahdenperä, Jaqueline S. J. Tan, Aroonroj Mekareeya, Robert S. Paton & Martin D. Smith.Angew. Chem. Int. Ed. 2019, 58, 2795. Direct Sulfonylation of Anilines Mediated by Visible Light Tarn C. Johnson, Bryony L. Elbert, Alistair J. M. Farley, Timothy W. Gorman, Christophe Genicot, Bénédicte Lallemand, Patrick Pasau, Jakub Flasz, José L. Castro, Malcolm MacCoss, Darren J. Dixon, Robert S. Paton, Christopher J. Schofield, Martin D. Smith & Michael C. Willis.Chem. Sci. 2018, 9, 629. Discovery of a Highly Selective Cell-active Inhibitor of KDM2/7 Philip A. Gerken, Jamie R. Wolstenhulme, Anthony Tumber, Stephanie B. Hatch, Yijia Zhang, Susanne Müller, Shane A. Chandler, Barbara Mair, Fengling Li,Sebastian M. B. Nijman, Rebecca Konietzny, Tamas Szommer, Clarence Yapp, Oleg Federov, Justin L. P. Benesch, Masoud Vedadi, Benedikt M. Kessler, Akane Kawamura, Paul E. Brennan & Martin D. Smith.Angew. Chem. Int. Ed. 2017, 56, 15555. A C-H Cyanation of 6-Ring N-Containing Heteroaromatics Bryony L. Elbert, Alistair J. M. Farley, Timothy W. Gorman, Tarn C. Johnson, Christophe Genicot, Bénédicte Lallemand, Patrick Pasau, Jakub Flasz, José L. Castro, Malcolm MacCoss, Robert S. Paton, Christopher J. Schofield, Martin D. Smith, Michael C. Willis & Darren J. Dixon.Chemistry Eur. J. 2017, 23, 14733-14737. Visible Light Photocatalysis of 6π Heterocyclization Niels Münster, Nicholas Parker, Lucy van Dijk, Robert S. Paton & Martin D. Smith.Angew. Chem. Int. Ed. 2017, 56, 9468-9472. Neutral Iodotriazole Foldamers as Tetradentate Halogen Bonding Anion Receptors Arseni Borrisov, J. Y. C. Lim, K. E. Christensen, Amber L. Thompson, Martin D. Smith & Paul D. Beer Chem. Commun. 2017, 53, 2483. Catalytic Enantioselective Synthesis of Atropisomeric Biaryls by a Cation-Directed O-Alkylation John D. Jolliffe, Roly J. Armstrong & Martin D. Smith.Nature Chem. 2017, 9, 558. A Cascade Strategy Enables a Total Synthesis of Morphine Shuyu Chu, Niels Munster, Tudor Balan & Martin D. Smith.Angew. Chem. Int. Ed. 2016, 55, 14306-14309. A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes Emily Kiss, Craig D. Campbell, Russell W. Driver, John D. Jolliffe, Rosemary Lang, Tetiana Sergeieva, Sergiy Okovytyy, Robert S. Paton & Martin D. Smith.Angew. Chem. Int. Ed. 2016, 55, 13813-13817. Catalytic Enantioselective Synthesis of C1 and C2-Symmetric Spirobiindanones Through Counterion-Directed Enolate C-Acylation Benjamin F. Rahemtulla, Hugh F. Clark & Martin D. Smith.Angew. Chem. Int. Ed. 2016, 55, 13180-13183. Torsional and Electronic Factors Control the C-H···O Interaction Russell W. Driver, Timothy D. W. Claridge, Steve Scheiner & Martin D. Smith.Chem. Eur. J. 2016, 22, 16513-16521.