Matthew OBrien

Biography

I was appointed to a lectureship in organic chemistry at Keele in the summer of 2012, moving here from Cambridge University where I was a fellow and Director-of-Studies for Natural Sciences at Pembroke College.

I was an undergraduate at York University and, after graduating, took up an industrial position as a medicinal synthetic chemist at Zeneca (now AstraZeneca) Pharmaceuticals. I returned to academia to study for a PhD under the supervision of Professor Jim Thomas at the University of Manchester where I worked towards the total-synthesis of the bryostatin family of natural products.

After a Post-Doctoral research period working with Professor Ian Paterson FRS in Cambridge on the total-synthesis of the marine macrolide discodermolide I was appointed as the Kinerton Lecturer of Organic Chemistry at Trinity College Dublin. My main research focus in Dublin was remote asymmetry, particularly the use of spiroketal scaffolds to facilitate long range asymmetric induction.

After 3 years in Dublin I returned to the UK to work with Professor Steven V. Ley CBE FRS in Cambridge where I was appointed as a fellow of Pembroke College. Aside from working on the Total-Synthesis of natural products, I invented a new method (using the Teflon AF-2400 gas permeable membrane) of using gases for synthetic chemistry in continuous flow.

Research and scholarship

Our research is focused on two key themes.

In addition to the generation of novel stereoselective synthetic methodologies and the total synthesis of biologically active natural products, we are also very interested in the development of new enabling technologies for automated chemical synthesis, particularly in the area of continuous-flow chemistry. A recent example of this is a continuous-flow inline liquid-liquid extraction system that uses a computer-vision approach (OpenCV/Python) to control the position of the interface (link: http://pubs.rsc.org/en/Content/ArticleLanding/2012/OB/c2ob25912e#!divAbstract).

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Teaching

CHE20001: Organic Synthesis and Catalysis
CHE20012: Drugs of Abuse
CHE20029: Radicals, Phases and Supramolecular Chemistry (Module Leader)
CHE30002/40/41: Chemistry and Medicinal Chemistry Research Projects
CHE30010: Forensic Toxicology
CHE30029: Forensic Science Dissertation
CHE30037: Topics in Chemistry
CHE30039: Advanced Organic Chemistry (Module Leader)

Selected Publications

Fitzpatrick DE, O'Brien M, Ley SV. 2020. A tutored discourse on microcontrollers, single board computers and their applications to monitor and control chemical reactions. REACTION CHEMISTRY & ENGINEERING, vol. 5(2), 201-220. link> doi> full text>
Dimitriou E, Jones RH, Pritchard RG, Miller GJ, O'Brien M. 2018. Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold. TETRAHEDRON, vol. 74(47), 6795-6803. link> doi> full text>
O'Brien M, Weber A, Hardy G, Ley SV. 2018. Highly diastereoselective boron and titanium mediated aldol reactions of a mannitol derived 2,3-butanediacetal ethyl ketone. TETRAHEDRON, vol. 74(38), 5319-5329. link> doi> full text>
O'Brien M, Hall A, Schrauwen J, van der Made J. 2018. An open-source approach to automation in organic synthesis: The flow chemical formation of benzamides using an inline liquid-liquid extraction system and a homemade 3-axis autosampling/product-collection device. TETRAHEDRON, vol. 74(25), 3152-3157. link> doi> full text>
O'Brien M and Polyzos A. 2018. Gaseous Reagents in Continuous-Flow Synthesis. In Flow Chemistry in Organic Synthesis. Jamison T and Koch G (Eds.). Thieme. doi> link>

Full Publications List show

Journal Articles

Fitzpatrick DE, O'Brien M, Ley SV. 2020. A tutored discourse on microcontrollers, single board computers and their applications to monitor and control chemical reactions. REACTION CHEMISTRY & ENGINEERING, vol. 5(2), 201-220. link> doi> full text>
Dimitriou E, Jones RH, Pritchard RG, Miller GJ, O'Brien M. 2018. Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold. TETRAHEDRON, vol. 74(47), 6795-6803. link> doi> full text>
O'Brien M, Weber A, Hardy G, Ley SV. 2018. Highly diastereoselective boron and titanium mediated aldol reactions of a mannitol derived 2,3-butanediacetal ethyl ketone. TETRAHEDRON, vol. 74(38), 5319-5329. link> doi> full text>
O'Brien M, Hall A, Schrauwen J, van der Made J. 2018. An open-source approach to automation in organic synthesis: The flow chemical formation of benzamides using an inline liquid-liquid extraction system and a homemade 3-axis autosampling/product-collection device. TETRAHEDRON, vol. 74(25), 3152-3157. link> doi> full text>
O'Brien M. 2017. An automated colorimetric inline titration of CO2 concentrations in solvent flow streams using a Teflon AF-2400 tube-in-tube device. JOURNAL OF CO2 UTILIZATION, vol. 21, 580-588. link> doi> full text>
O'Brien M, Konings L, Martin M, Heap J. 2017. Harnessing open-source technology for low-cost automation in synthesis: Flow chemical deprotection of silyl ethers using a homemade autosampling system. TETRAHEDRON LETTERS, vol. 58(25), 2409-2413. link> doi> full text>
Cooper DA, Robbins E, Tizzard GJ, Coles SJ, O'Brien M. 2017. Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans. Journal of Organic Chemistry. link> doi> link> full text>
O'Brien M, Cooper DA, Dolan J. 2017. Continuous flow iodination using an automated computer-vision controlled liquid-liquid extraction system. TETRAHEDRON LETTERS, vol. 58(9), 829-834. link> doi> full text>
Ball M, Baron A, Bradshaw B, Dumeunier R, O'Brien M, Thomas EJ. 2016. The evolution of a stereoselective synthesis of the C1-C16 fragment of bryostatins. Organic and Biomolecular Chemistry, 9650-9681. doi> link>
O'Brien M, Cooper DA, Mhembere P. 2016. The continuous-flow synthesis of carbazate hydrazones using a simplified computer-vision controlled liquid-liquid extraction system. TETRAHEDRON LETTERS, vol. 57(47), 5188-5191. link> doi> full text>
O'Brien M. 2016. Creating 3-Dimensional Molecular Models to Help Students Visualize Stereoselective Reaction Pathways. JOURNAL OF CHEMICAL EDUCATION, vol. 93(9), 1663-1666. link> doi> full text>
O'Brien M and Cooper D. 2016. Continuous Flow Liquid-Liquid Separation Using a Computer-Vision Control System: The Bromination of Enaminones with N-Bromosuccinimide. SYNLETT, vol. 27(1), 164-168. link> doi> link> full text>
Brzozowski M, O'Brien M, Ley SV, Polyzos A. 2015. Flow chemistry: intelligent processing of gas-liquid transformations using a tube-in-tube reactor. Accounts of Chemical Research, vol. 48(2), 349-362. link> doi> link>
Gross U, Koos P, O'Brien M, Polyzos A, Ley SV. 2014. A General Continuous Flow Method for Palladium Catalysed Carbonylation Reactions Using Single and Multiple Tube-in-Tube Gas-Liquid Microreactors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 6418-6430. link> doi> link>
Pastre JC, Browne DL, O'Brien M, Ley SV. 2013. Scaling Up of Continuous Flow Processes with Gases Using a Tube-in-Tube Reactor: Inline Titrations and Fanetizole Synthesis with Ammonia. ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 17(9), 1183-1191. link> doi>
Ley SV, Ingham RJ, O'Brien M, Browne DL. 2013. Camera-enabled techniques for organic synthesis. Beilstein J Org Chem, vol. 9, 1051-1072. link> doi>
Bourne SL, O'Brien M, Kasinathan S, Koos P, Tolstoy P, Hu DX, Bates RW, Martin B, Schenkel B, Ley SV. 2013. Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes. CHEMCATCHEM, vol. 5(1), 159-172. link> doi>
Kraus H, Francais A, O'Brien M, Frost J, Dieguez-Vazquez A, Polara A, Baricordi N, Horan R, Hsu D-S, Tsunoda T, Ley SV. 2013. Synthesis of spongistatin 2 employing a new route to the EF fragment. CHEMICAL SCIENCE, vol. 4(5), 1989-1994. link> doi>
Hu DX, O'Brien M, Ley SV. 2012. Continuous multiple liquid-liquid separation: diazotization of amino acids in flow. Org Lett, vol. 14(16), 4246-4249. link> doi>
O'Brien M, Koos P, Browne DL, Ley SV. 2012. A prototype continuous-flow liquid-liquid extraction system using open-source technology. Org Biomol Chem, vol. 10(35), 7031-7036. link> doi>
Browne DL, O'Brien M, Koos P, Cranwell PB, Polyzos A, Ley SV. 2012. Continuous-Flow Processing of Gaseous Ammonia Using a Teflon AF-2400 Tube-in-Tube Reactor: Synthesis of Thioureas and In-Line Titrations. SYNLETT, 1402-1406. link> doi>
Cranwell PB, O'Brien M, Browne DL, Koos P, Polyzos A, Peña-López M, Ley SV. 2012. Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal-Knorr pyrrole formation and gas concentration measurement by inline flow titration. Org Biomol Chem, vol. 10(30), 5774-5779. link> doi>
O'Brien M, Leach A, Armstrong RJ, Chong K, Sheridan R. 2012. Furanyl cyclic amines: a diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control. Org Biomol Chem, vol. 10(12), 2392-2394. link> doi>
Petersen TP, Polyzos A, O'Brien M, Ulven T, Baxendale IR, Ley SV. 2012. The oxygen-mediated synthesis of 1,3-butadiynes in continuous flow: using Teflon AF-2400 to effect gas/liquid contact. ChemSusChem, vol. 5(2), 274-277. link> doi>
O'Brien M and Thomas EJ. 2011. Synthesis of the C(1)-C(16) fragment of bryostatins using an 'ene' reaction between an allylsilane and an alkynone. TETRAHEDRON, vol. 67(52), 10068-10081. link> doi>
Kasinathan S, Bourne SL, Tolstoy P, Koos P, O'Brien M, Bates RW, Baxendale IR, Ley SV. 2011. Syngas-Mediated C-C Bond Formation in Flow: Selective Rhodium-Catalysed Hydroformylation of Styrenes. SYNLETT, 2648-2651. link> doi>
Bourne SL, Koos P, O'Brien M, Martin B, Schenkel B, Baxendale IR, Ley SV. 2011. The Continuous-Flow Synthesis of Styrenes Using Ethylene in a Palladium-Catalysed Heck Cross-Coupling Reaction. SYNLETT, 2643-2647. link> doi>
Koos P, Gross U, Polyzos A, O'Brien M, Baxendale I, Ley SV. 2011. Teflon AF-2400 mediated gas-liquid contact in continuous flow methoxycarbonylations and in-line FTIR measurement of CO concentration. Org Biomol Chem, vol. 9(20), 6903-6908. link> doi>
Lupo G, Gestri G, O'Brien M, Denton RM, Chandraratna RAS, Ley SV, Harris WA, Wilson SW. 2011. Retinoic acid receptor signaling regulates choroid fissure closure through independent mechanisms in the ventral optic cup and periocular mesenchyme. Proc Natl Acad Sci U S A, vol. 108(21), 8698-8703. link> doi>
O'Brien M, Denton R, Ley SV. 2011. Lesser-Known Enabling Technologies for Organic Synthesis. SYNTHESIS-STUTTGART, 1157-1192. link> doi>
Polyzos A, O'Brien M, Petersen TP, Baxendale IR, Ley SV. 2011. The continuous-flow synthesis of carboxylic acids using CO2 in a tube-in-tube gas permeable membrane reactor. Angew Chem Int Ed Engl, vol. 50(5), 1190-1193. link> doi>
O'Brien M, Taylor N, Polyzos A, Baxendale IR, Ley SV. 2011. Hydrogenation in flow: Homogeneous and heterogeneous catalysis using Teflon AF-2400 to effect gas-liquid contact at elevated pressure. CHEMICAL SCIENCE, vol. 2(7), 1250-1257. link> doi>
O'Brien M and Burley GA. 2010. Highlights from the 45th EUCHEM Conference on Stereochemistry, Bürgenstock, Switzerland, May 2010. Chem Commun (Camb), vol. 46(42), 7868-7871. link> doi>
O'Brien M, Baxendale IR, Ley SV. 2010. Flow ozonolysis using a semipermeable Teflon AF-2400 membrane to effect gas-liquid contact. Org Lett, vol. 12(7), 1596-1598. link> doi>
Carter CF, Baxendale IR, O'Brien M, Pavey JBJ, Ley SV. 2009. Synthesis of acetal protected building blocks using flow chemistry with flow I.R. analysis: preparation of butane-2,3-diacetal tartrates. Org Biomol Chem, vol. 7(22), 4594-4597. link> doi>
Evans P, Kavanagh Y, O'Brien M. 2009. Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton. Tetrahedron, vol. 65(39), 8259-8268. doi>
O'Brien M, Cahill S, Evans LA. 2008. A diastereoselective route to 2,6-syn-disubstituted tetrahydropyrans: synthesis of the civet compound (+)-2-((2S,6S)-6-methyltetrahydro-2H-pyran-2-yl) acetic acid. Chem Commun (Camb), 5559-5561. link> doi>
Bridgwood KL, Tzschucke CC, O'Brien M, Wittrock S, Goodman JM, Davies JE, Logan AWJ, Hüttl MRM, Ley SV. 2008. Enantiopure 2-substituted glyceraldehyde derivatives by aza-Claisen rearrangement or C-alkylation of enamines. Org Lett, vol. 10(20), 4537-4540. link> doi>
O'Brien M, Diéguez-Vázquez A, Hsu D-S, Kraus H, Sumino Y, Ley SV. 2008. Azeotropic reflux chromatography: an efficient solution to a difficult separation in the scale-up synthesis of spongistatin 1. Org Biomol Chem, vol. 6(7), 1159-1164. link> doi>
Cahill S, Evans LA, O'Brien M. 2007. Furanyl spiroketals as stereochemical relays in the synthesis of 1,9-anti diols: synthesis of insect pheromones. Tetrahedron Letters, vol. 48(32), 5683-5686. doi>
Cahill S and O'Brien M. 2006. Furanyl spiroketals: thermodynamic control of remote asymmetry. Tetrahedron Letters, vol. 47(22), 3665-3668. doi>
Paterson I, Delgado O, Florence GJ, Lyothier I, O'Brien M, Scott JP, Sereinig N. 2005. A second-generation total synthesis of (+)-discodermolide: the development of a practical route using solely substrate-based stereocontrol. J Org Chem, vol. 70(1), 150-160. link> doi>
O'Brien M, Taylor NH, Thomas EJ. 2002. Synthesis of the C(1)-C(16) fragment of bryostatins. TETRAHEDRON LETTERS, vol. 43(31), 5491-5494. link> doi>
Davies DT, Goodall K, Kapur N, OBrien M, Parsons AF. 1997. The synthesis of dehydroamino acids from pyruvic acid. SYNTHETIC COMMUNICATIONS, vol. 27(21), 3815-3822. link> doi>

Chapters

O'Brien M and Polyzos A. 2018. Gaseous Reagents in Continuous-Flow Synthesis. In Flow Chemistry in Organic Synthesis. Jamison T and Koch G (Eds.). Thieme. doi> link>
O'Brien M, Ley S, Browne D. 2018. Immobilized Reagents and Multistep Processes. In Flow Chemistry in Organic Synthesis. Jamison T and Koch G (Eds.). Thieme. doi> link>
Hancock LM, Edwards MG, Jones GR, O'Brien M. 2017. Cram's Rule: Diastereoselective Grignard addition to 2-phenylpropanal. In Comprehensive Organic Chemistry Experiments for the Laboratory Classroom. Alfonso CAM, Candeias NR, Simao DP, Trindade AF, Coelho JAS, Tan B, Franzen R (Eds.). Royal Society of Chemistry.

Other

Baron A, Ball M, Bradshaw B, Donnelly S, Germay O, Oller PC, Kumar N, Martin N, O'Brien M, Omori H, Moore C, Thomas EJ. 2005. Approaches to the stereoselective total synthesis of biologically active natural products. PURE AND APPLIED CHEMISTRY (vol. 77, pp. 103-117). link> doi>

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Dr Matthew O'Brien