Dr Mark Elliott
Senior Lecturer in Organic Chemistry
- elliottmc@cardiff.ac.uk
- +44 (0)29 2087 4686
- Fax:
- +44 (0)29 2087 4030
Trosolwg
Links
Research Group: Biological and Organic Chemistry
Research Interests
Dr Elliott's research interests are in the areas of heterocyclic chemistry, asymmetric synthesis and natural product synthesis.
Much of our work has focused on the stereoselective annulation of azoline derivatives, including oxazolines, thiazolines and pyrrolidines. This has led to the discovery of a number of new synthetic transformations, all of which can be applied to targets of biological interest. Recently, we have developed a range of stereoselective desymmetrisation reactions of cyclohexa-1,4-dienes, leading to the invention of methods for the preparation of bicyclic compounds containing challenging quaternary stereogenic centres. All of these fundamental areas are the subject of total synthesis endeavours, with the batzelladine and lycoposerramine alkaloids, and cladiellin diterpenes featuring prominently.
For more information, click on the 'Research' tab above.
Teaching
CH3203 Organic Chemistry of Multiply Bonded Systems
Bywgraffiad
PhD Loughborough University of Technology (1994, C. J. Moody). Postdoctoral Research Fellow, Basel and MÃ lheim (1994-6, A. Pfaltz). Appointed as Lecturer, Cardiff, in 1996.
Member of the Royal Society of Chemistry and Chartered Chemist. Member of the International Editorial Advisory Board of the journals 'Heterocyclic Communications' and 'Heterocyclic Letters'. Dr Elliott regularly referees manuscripts for a broad range of journals, including 'Journal of Organic Chemistry', 'Organic and Biomolecular Chemistry', 'Chemical Communications', 'Tetrahedron', 'Tetrahedron Letters' and 'Synlett' (among others).
Cyhoeddiadau
2021
- Smith, K., Saleh, B. A., Alshammari, M. B., El-Hiti, G. A. and Elliott, M. 2021. Studies on a catalytic version of the Matteson asymmetric homologation reaction. Organic and Biomolecular Chemistry(19), pp. 4279-4284. (10.1039/d1ob00604e)
- Saleh, B. A., Smith, K., Elliott, M. C. and El-Hiti, G. A. 2021. Reactions between lithiated 1,3-dithiane oxides and trialkylboranes. Journal of Sulfur Chemistry 42(6), pp. 591-603. (10.1080/17415993.2021.1971670)
2020
- Elliott, M. 2020. Laying the foundations, section 1 from Elliott: how to succeed in organic chemistry. In: Organic and Medicinal Chemistry. Oxford University Press, pp. 3-83.
- Elliott, M. C. 2020. How to succeed in organic chemistry. Oxford: Oxford University Press.
2018
- Smith, K., Al-Zuhairi, A. J., Elliott, M. C. and El-Hiti, G. A. 2018. Regioselective synthesis of important chlorophenols in the presence of methylthioalkanes with remote SMe, OMe or OH substituents. Journal of Sulfur Chemistry 39(6), pp. 607-621. (10.1080/17415993.2018.1493111)
2016
- Saleh, B. A., Smith, K., Elliott, M. C., Jones, D. H., Kariuki, B. M. and El Hiti, G. A. 2016. Reactions of organoboranes with carbanions bearing three potential leaving groups: unusual processes, products and mechanisms. Tetrahedron 72(44), pp. 6914-6928. (10.1016/j.tet.2016.09.005)
- Ghafoor, A. et al. 2016. Synthesis, characterization and biological evaluation of some new oxino bis-pyrazole derivatives. Asian Journal of Chemistry 28(8), pp. 1648-1652. (10.14233/ajchem.2016.19736)
2015
- Jones, D. H., Smith, K., Elliott, M. C. and El-Hiti, G. A. 2015. Factors affecting reactions of trialkylcyanoborates with imidoyl chlorides/trifluoroacetic anhydride. Tetrahedron 71(36), pp. 6285-6289. (10.1016/j.tet.2015.06.038)
- Elliott, M. C. and Saleh, B. A. 2015. Synthesis by substitution of metals. In: Aitken, R. A. et al. eds. Science of Synthesis Knowledge Updates 2015/2. Thieme, pp. 391-398.
- Saleh, B. A. and Elliott, M. C. 2015. Synthesis by substitution of carbon functionalities. In: Aitken, R. A. et al. eds. Science of Synthesis Knowledge Updates 2015/2. Thieme, pp. 399-414.
2014
- Maqbool, T. et al. 2014. Pyrazolopyridines II: synthesis and antibacterial screening of 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids. Asian Journal of Chemistry 26(10), pp. 2870-2872. (10.14233/ajchem.2014.15918)
- Elliott, M. C. and Jones, D. H. 2014. [4 + 2] Cycloaddition as the key step. In: Muller, T. J. J. ed. Multicomponent Reactions 2. Reactions Involving an a,b-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron-, Silicon-, Free-Radical-, and Metal-Mediated Reactions. Düsseldorf: Thieme, pp. 243-286.
- Elliott, M. C. and Hewitt, N. L. 2014. Partial reduction of benzenoid aromatic rings by dissolving metals and by other methods. In: Reference module in chemistry, molecular sciences and chemical engineering: Comprehensive Organic Synthesis II., Vol. 8. Elsevier, pp. 639-672., (10.1016/B978-0-08-097742-3.00821-1)
2013
- El-Hiti, G. A., Smith, K., Elliott, M. C., Jones, D. H. and Kariuki, B. 2013. (E)-2-(1,1-Dicyclohexyl-3-phenylallyl)-5,5-dimethyl-1,3,2-dioxaborinane. Acta Crystallographica Section E - Structure Reports Online 69(9), article number: o1403. (10.1107/S1600536813021739)
- Elliott, M. C., Smith, K., Jones, D. H., Hussain, A. and Saleh, B. A. 2013. Factors affecting migration of tertiary alkyl groups in reactions of alkylboronic esters with bromomethyllithium. The Journal of Organic Chemistry 78(7), pp. 3057-3064. (10.1021/jo4000459)
- Elliott, M. C. and Smith, K. 2013. Migratory aptitudes of alkyl groups on boron: a computational study of halomethyllithium-induced migration reactions. Organometallics 32(17), pp. 4878-4881. (10.1021/om4006164)
- Smith, K., Elliott, M. C. and Jones, D. H. 2013. 3-Chloro-1-lithiopropene - a functional organolithium reagent - and its reactions with alkylboronates to give 3-Alkylprop-1-en-3-ols. Journal of Organic Chemistry 78(18), pp. 9526-9531. (10.1021/jo4018028)
- Maqbool, T. et al. 2013. Pyrazolopyridines I: Synthesis of some pyrazolo[3,4-b]pyridine-4-carboxylates. Asian Journal of Chemistry 25(14), pp. 7715-7718. (10.14233/ajchem.2013.14573A)
2012
- Butters, M., Elliott, M. C. and Hill-Cousins, J. T. 2012. An unexpected Prins desymmetrisation reaction driven by silyl migration. Arkivoc Online Journal of Organic Chemistry 2012(7), pp. 113-125.
- Bennett, N. J., Elliott, M. C., Hewitt, N. L., Kariuki, B., Morton, C. A., Raw, S. A. and Tomasi, S. 2012. Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid. Organic and Biomolecular Chemistry 10(19), pp. 3859-3865. (10.1039/c2ob25211b)
2011
- Altug, C. et al. 2011. An efficient one-pot multicomponent approach to 5-amino-7-aryl-8-nitrothiazolo[3,2-a]pyridines. Tetrahedron 67(49), pp. 9522-9528. (10.1016/j.tet.2011.10.005)
2010
- Altug, C., Dürüst, Y., Elliott, M. C., Kariuki, B., Rorstad, T. and Zaal, M. 2010. Reaction of heterocyclic enamines with nitrile oxide and nitrilimine precursors. Organic & Biomolecular Chemistry 8(21), pp. 4978-4986. (10.1039/c0ob00286k)
2009
- Altug, C., Durust, Y., Elliott, M. C. and Kariuki, B. 2009. Tandem nitrosation/cycloaddition of heterocyclic enamines using nitrolic acids. Tetrahedron Letters 50(34), pp. 4919-4921. (10.1016/j.tetlet.2009.06.065)
- Elliott, M. C. and Paine, J. S. 2009. Studies towards the total synthesis of lycoposerramine A. Synthesis of a model for the tetracyclic core. Organic & Biomolecular Chemistry 7(17), pp. 3455-3462. (10.1039/b909860g)
- Butters, M. et al. 2009. Synthesis and stereochemical determination of batzelladine C methyl ester. Organic & Biomolecular Chemistry 7(23), pp. 5001-5009. (10.1039/b914744f)
- Altug, C., Dürüst, Y. and Elliott, M. C. 2009. Reactions of alkylidenepyrrolidines with alpha-chlorooximes and alpha-chlorohydrazones. Tetrahedron Letters 50(52), pp. 7392-7394. (10.1016/j.tetlet.2009.10.086)
2008
- Butters, M., Beetstra, D. J., Elliott, M. C., Hill-Cousins, J. T. and Kariuki, B. 2008. Directed epoxidation of cyclohexa-1,4-dienes-stereoselective formation of up to six contiguous stereogenic centres. Organic & Biomolecular Chemistry 6(23), pp. 4426-4434. (10.1039/b814131m)
- Butters, M., Elliott, M. C., Hill-Cousins, J. T., Paine, J. S. and Westwood, A. W. J. 2008. An improved protocol for the Prins desymmetrization of cyclohexa-1,4-dienes. Tetrahedron Letters 49(28), pp. 4446-4448. (10.1016/j.tetlet.2008.05.022)
- Davies, C. D., Elliott, M. C., Hill-Cousins, J., Khan, M. U. A., Maqbool, T. and Wood, J. L. 2008. A concise diastereoselective approach to the left-hand side of batzelladine A. Synlett(13), pp. 2028-2032. (10.1055/s-2008-1077969)
- Elliott, M. C., El Sayed, N. N. E. and Paine, J. S. 2008. Concise synthesis of the tricyclic core of lycoposerramine S. Organic & Biomolecular Chemistry 6(14), pp. 2611-2618. (10.1039/b804664f)
- Elliott, M. C. 2008. Bicyclic 5-6 Systems: Four Heteroatoms 1:3. In: Jones, R. C. F. ed. Comprehensive Heterocyclic Chemistry III., Vol. 10. Amsterdam: Elsevier, pp. 493-509., (10.1016/B978-008044992-0.00909-3)
2007
- Elliott, M. C., El Sayed, N. N. E. and Paine, J. S. 2007. Diastereospecific tandem Prins cyclisation/rearrangement reactions for the desymmetrisation of cyclohexa-1,4-dienes. European Journal of Organic Chemistry 2007(5), pp. 792-803. (10.1002/ejoc.200600928)
- Butters, M., Elliott, M. C., Hill-Cousins, J., Paine, J. S. and Walker, J. K. E. 2007. Iodocyclization Reactions for the Desymmetrization of Cyclohexa-1,4-dienes. Organic Letters 9(18), pp. 3635 -3638. (10.1021/ol701492g)
- Elliott, M. C., El Sayed, N. N. and Ooi, L. 2007. Sulfoxide-directed desymmetrisation of cyclohexa-1,4-dienes. Tetrahedron Letters 48(26), pp. 4561-4564. (10.1016/j.tetlet.2007.04.138)
- Elliott, M. C. and Paine, J. S. 2007. 1R,1¢R)-1,1¢,2,2¢,3,3¢,4,4¢-Octahydro-1,1¢-biisoquinoline. In: Paquette, L. A. ed. e-EROS Encyclopedia of Reagents for Organic Synthesis. Chichester: Wiley-Blackwell
2006
- Davies, C. D., Elliott, M. C. and Wood, J. L. 2006. Acylation of alkylidenepyrrolidines with heterocumulenes - a reinvestigation. Tetrahedron 62(48), pp. 11158-11164. (10.1016/j.tet.2006.09.014)
- Cavell, K. J., Elliott, M. C., Nielsen, D. J. and Paine, J. S. 2006. Chiral N-heterocyclic carbene ligands based on a biisoquinoline template. Dalton Transactions(41), pp. 4922-4925. (10.1039/b611647g)
- Elliott, M. C. and Wordingham, S. V. 2006. A Convenient Protocol for the Alkylidenation of Lactams. Synthesis 2006(7), pp. 1162-1170. (10.1055/s-2006-926390)
2005
- Beutler, A., Davies, C. D., Elliott, M. C., Galea, N., Long, M. S., Willock, D. J. and Wood, J. L. 2005. Diastereoselective Dimerisation of Alkenylthiazolines: A Combined Synthetic and Computational Study. European Journal of Organic Chemistry 2005(17), pp. 3791-3800. (10.1002/ejoc.200500360)
- Elliott, M. C. and El-Sayed, N. . N. 2005. Stereodivergent radical cyclisation reactions of cyclohexa-1,4-dienes. Tetrahedron Letters 46(17), pp. 2957-2959. (10.1016/j.tetlet.2005.03.042)
- Elliott, M., Wood, J. L. and Wordingham, S. V. 2005. Alkylidenepyrrolidines: Synthesis and Applications in Heterocyclic Chemistry. Trends in Heterocyclic Chemistry 10, pp. 73-95.
- Elliott, M. C. 2005. Imines and their N-substituted derivatives: hydrazones and other N,N-derivatives including diazo compounds. In: Katritzky, A. R. and Taylor, R. J. K. eds. Comprehensive Organic Functional Group Transformations II., Vol. 3. Amsterdam: Elsevier, pp. 469-523., (10.1016/B0-08-044655-8/00057-X)
2004
- Jackstell, R. et al. 2004. An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols. Chemistry - a European Journal 10(16), pp. 3891-3900. (10.1002/chem.200400182)
- Elliott, M. C. and Long, M. S. 2004. Studies towards the total synthesis of batzelladine A. Organic & Biomolecular Chemistry 2(14), pp. 2003-2011. (10.1039/b404679j)
- Elliott, M. C., Gist, M. J., Binns, F. and Jones, R. G. 2004. A convenient synthesis of 2-methyl-3-oxoheptane-1,7-dicarboxylic esters and amides. Tetrahedron Letters 45(14), pp. 2899-2901. (10.1016/j.tetlet.2004.02.067)
- Elliott, M. C. and Wordingham, S. V. 2004. Reversibility in Lewis-acid Promoted Reactions of N-Arylcinnamamides. Synlett 2004(5), pp. 898-900. (10.1055/s-2004-820024)
- Elliott, M. C., Malik, K. M. A. and Williams, E. 2004. Crystal structures and conformations of two new biisoquinoline derivatives. Journal of Chemical Crystallography 34(6), pp. 371-381. (10.1023/B:JOCC.0000028669.22883.be)
2003
- Elliott, M. C. and Williams, E. 2003. Synthesis and reactions of partially reduced biisoquinolines. Organic & Biomolecular Chemistry 1(17), pp. 3038-3047. (10.1039/b306159k)
2002
- Elliott, M. C. and Long, M. S. 2002. Studies towards the total synthesis of Batzelladine A: synthesis of a model pyrrolo[1,2-c]pyrimidine. Tetrahedron Letters 43(50), pp. 9191-9194. (10.1016/S0040-4039(02)02261-X)
- Elliott, M. C. 2002. Saturated oxygen heterocycles. Journal of the Chemical Society, Perkin Transactions 1 2002(21), pp. 2301-2323. (10.1039/b201515n)
- Elliott, M. C., Williams, E. and Howard, S. T. 2002. Synthesis and properties of a chiral bis-tetrahydroisoquinoline proton sponge. Journal of the Chemical Society, Perkin Transactions 2 2002(2), pp. 201-203. (10.1039/b110499n)
2001
- Elliott, M. C., Kruiswijk, E. and Willock, D. J. 2001. Asymmetric hetero-Diels-Alder reactions. Reactions of oxazolo[3,2-c]pyrimidines. Tetrahedron 57(51), pp. 10139-10146. (10.1016/S0040-4020(01)01032-8)
- Elliott, M. C., Kruiswijk, E. and Long, M. S. 2001. Annulation reactions of azoles and azolines with heterocumulenes. Tetrahedron 57(31), pp. 6651-6677. (10.1016/S0040-4020(01)00442-2)
- Elliott, M. C., Galea, N., Long, M. S. and Willock, D. J. 2001. Highly diastereoselective dimerisation of alkenylthiazolines. Tetrahedron Letters 42(29), pp. 4937-4939. (10.1016/S0040-4039(01)00886-3)
- Elliott, M. C. and Williams, E. 2001. Saturated oxygen heterocycles. Journal of the Chemical Society, Perkin Transactions 1 2001(19), pp. 2303-2340. (10.1039/b007290g)
2000
- Loiseleur, O., Elliott, M. C., Von Matt, P. and Pfaltz, A. 2000. Pd-Catalyzed allylic substitution with enantiomerically pure catalysts and chiral non-racemic substrates: A new approach to catalyst-based regiocontrol, preliminary communication. Helvetica Chimica Acta 83(9), pp. 2287-2294. (10.1002/1522-2675(20000906)83:9<2287::AID-HLCA2287>3.0.CO;2-J)
- Elliott, M. C. 2000. Saturated oxygen heterocycles. Journal of the Chemical Society, Perkin Transactions 1 2000(9), pp. 1291-1318. (10.1039/a903885j)
1999
- Elliott, M. C. and Kruiswijk, E. 1999. Asymmetric hetero-Diels-Alder reactions of alkenyldihydrooxazoles. Synthesis of oxazolo[3,2-c]pyrimidines and related compounds. Journal of the Chemical Society, Perkin Transactions 1 1999(21), pp. 3157-3166. (10.1039/a905700e)
- Elliott, M. C., Monk, A. E., Kruiswijk, E., Hibbs, D. E., Jenkins, R. L. and Jones, D. V. 1999. Asymmetric Hetero-Diels-Alder Reactions with Heterocumulenes. Synlett 1999(9), pp. 1379-1382. (10.1055/s-1999-2853)
1998
- Elliott, M. C., Kruiswijk, E. and Willock, D. J. 1998. Asymmetric hetero-Diels-Alder reactions. Mechanism of the reaction of alkenyloxazolines with isocyanates. Tetrahedron Letters 39(48), pp. 8911-8914. (10.1016/S0040-4039(98)01949-2)
- Elliott, M. C. 1998. Saturated oxygen heterocycles. Journal of the Chemical Society, Perkin Transactions 1 1998(24), pp. 4175-4200. (10.1039/a805170d)
- Elliott, M. C., Hibbs, D. E., Hughes, D. S., Hursthouse, M. B., Kruiswijk, E. and Malik, K. M. A. 1998. Asymmetric hetero-Diels-Alder reactions: X-ray structures of three novel chiral dihydropyrimidines. Journal of Chemical Crystallography 28(9), pp. 663-671. (10.1023/A:1021791832534)
1997
- Moody, C. J., Doyle, K. J., Elliott, M. C. and Mowlem, T. J. 1997. Studies towards the synthesis of diazonamide A. Unexpected formation of a 3,4-bridged indole. Journal of the Chemical Society, Perkin Transactions 1 1997(16), pp. 2413-2420. (10.1039/a700684e)
- Elliott, M. C. 1997. Saturated oxygen heterocycles. Contemporary Organic Synthesis 4(3), pp. 238-259. (10.1039/co9970400238)
- Elliott, M. C. and Kruiswijk, E. 1997. Highly diastereoselective hetero-Diels-Alder reactions of alkenyldihydrooxazoles as an approach to novel pyrimidine derivatives. Chemical Communications 1997(23), pp. 2311-2312. (10.1039/a705571d)
1995
- Brown, D. S., Elliott, M. C., Moody, C. J. and Mowlem, T. J. 1995. Preparation of oxonanes and azonanes by oxidative ring expansion: synthesis of obtusan. Journal of the Chemical Society, Perkin Transactions 1 1995(9), pp. 1137-1144. (10.1039/p19950001137)
1994
- Elliott, M. C. 1994. Recent developments in the synthesis of medium-ring ethers. Contemporary Organic Synthesis 1(6), pp. 457-474. (10.1039/co9940100457)
- Brown, D. S., Elliott, M. C., Moody, C. J., Mowlem, T. J., Marino, J. P. J. and Padwa, A. 1994. Ligand effects in the Rhodium(II)-catalyzed reactions of α-diazoamides. Oxindole formation is promoted by the use of Rhodium(II) perfluorocarboxamide catalysts. The Journal of Organic Chemistry 59(9), pp. 2447-2455. (10.1021/jo00088a028)
- Moody, C. J., Doyle, K. J., Elliott, M. C. and Mowlem, T. J. 1994. Synthesis of heterocyclic natural products: Model studies towards diazonamide A. Pure and Applied Chemistry 66(10-11), pp. 2107-2110. (10.1351/pac199466102107)
1993
- Elliott, M. C., Moody, C. J. and Mowlem, T. J. 1993. Preparation of 9-Membered Cyclic Ethers from Phthalans. Synthesis of Obtusan. Synlett 1993(12), pp. 909-910. (10.1055/s-1993-22648)
Addysgu
Our research interests lie in the development of new synthetic methodology, and its application to target synthesis. Key areas include:
Stereoselective annulation reactions of pyrrolidine, oxazoline and thiazoline derivatives which provide access to a range of novel heterobicyclic systems.
Development of new desymmetrisation reactions of cyclohexadiene systems to provide highly complex carbocyclic and heterocyclic systems.
Recent highlights include the total synthesis of batzelladine C methyl ester 2 from succinimide 1, permitting the stereochemical assignment of this challenging natural product.
Lycoposerramine A is a complex alkaloid featuring a pentacyclic core with five stereogenic centres and an unprecedented (in natural products) spirocyclic oxadiazolidinone ring. Compound 4 was prepared in only 7 steps from cyclohexadiene 3 as a highly functionalised model for this core.
A further application of cyclohexa-1,4-diene chemistry is shown in the highly efficient Prins desymmetrisation of compound 5 to give product 6 which is structurally and stereochemically related to the cladiellin diterpenes.
One final highlight from our recent work is the conversion of alkylidenepyrroldine 7 into the adduct 8. This reaction proceeds by a one-pot multistep sequence involving trapping of the nitrous acid that is liberated from the nitrolic acid, followed by decarboxylation and two dipolar cycloadditions (collaboration with Prof. Yasar Dà rà st, Abant Izzet Baysal University, Turkey).
