Publications

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Sheppard Group Research Publications

71. C. L. C. Smelt, V. R. Sanders, J. Newcombe, R. P. Burt, T. D. Sheppard, M. Topf, N. S. Millar, Identification by virtual screening and functional characterisation of novel positive and negative allosteric modulators of the α7 nicotinic acetylcholine receptor, Neuropharmacology 2018, 139, 194. doi: 10.1016/j.neuropharm.2018.07.009

70. V. Karaluka, K. Murata, S. Masuda, Y. Shiramatsu, T. Kawamoto, H. C. Hailes, T. D. Sheppard, A. Kamimura, Development of a microwave-assisted sustainable conversion of furfural hydrazones to functionalised phthalimides in ionic liquids, RSC Advances 2018, 8, 22617. doi: 10.1039/C8RA03895C

69. H. R. Rzepa, S. Arkhipenko, E. Wan, M. T. Sabatini, V. Karaluka, A. Whiting, T. D. Sheppard, An Accessible Method for DFT Calculation of 11B NMR Shifts of Organoboron Compounds, The Journal of Organic Chemistry 2018, 83, 8020. doi: 10.1021/acs.joc.8b00859

68. M. Bawn, F. Subrizi, G. J. Lye, T. D. Sheppard, H. C. Hailes, J. M. Ward, One-pot, two-step transaminase and transketolase synthesis of L-gluco-heptulose from L-arabinose, Enzyme and Microbial Technology 2018, 116, 16. Open Access. doi: 10.1016/j.enzmictec.2018.05.006

67. S. M. Gibson, J. M. D'Oyley, J. I. Higham, K. Sanders, V. Laserna, A. E. Aliev, T. D. Sheppard, Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules, European Journal of Organic Chemistry 2018, 4018. Open Access. doi: 10.1002/ejoc.201800668

66. M. T. Sabatini, V. Karaluka, R. M. Lanigan, L. T. Boulton, M. Badland, T. D. Sheppard, Protecting group free amidation of amino acids using Lewis acid catalysts, Chemistry - A European Journal 2018, 24, 7033. Open Access. doi: 10.1002/chem.201800372

65. S. Arkhipenko, M. Sabatini, A. Batsanov, V. Karaluka, T. D. Sheppard, H. Rzepa. A. Whiting, Mechanistic insights into boron-catalysed direct amidation reactions, Chemical Science 2018, 9, 1058. Open Access. doi: 10.1039/C7SC03595K

64. C. E. Coomber, L. Benhamou, D. -K. Bucar, P. D. Smith, M. J. Porter, T. D. Sheppard, Silver-Free Palladium-Catalyzed C(sp3)–H Arylation of Saturated Bicyclic Amine Scaffolds, Journal of Organic Chemistry 2018, 83, 2495. Open Access. doi: 10.1021/acs.joc.7b02665

This article was featured on the journal cover, with a design by Tom, Charlotte and Mike upon a background photo of the 'Alpspitze' in the Bavarian alps taken by Tom.

63. J. Newcombe, A. Chatzidacki, T. D. Sheppard, M. Topf, N. S. Millar, Diversity of nicotinic acetylcholine receptor positive allosteric modulators revealed by mutagenesis and a revised structural model, Molecular Pharmacology 2018, 93, 128. Open Access. doi: 10.1124/mol.117.110551

This article was featured on the journal cover.

62. S. M. Gibson, D. Macmillan, T. D. Sheppard, Synthesis of boronocysteine, Synlett 2018, 314. UCL RPS link pdf doi: 10.1055/s-0036-1591491

61. M. T. Sabatini, L. T. Boulton, T. D. Sheppard, Borate esters: Simple catalysts for the sustainable synthesis of complex amides, Science Advances 2017, 3, e1701028. doi: 10.1126/sciadv.1701028 Open Access

This work was higlighted in Synform and highlighted in Some items of interest to Process R&D Chemists and Engineers in OPR&D.

60. S. I. Jacob, B. Khogeer, N. Bampos, T. D. Sheppard, R. M. Schwartz, C. R. Lowe, The development and application of synthetic affinity ligands for the purification of ferritin-based influenza antigens , Bioconjugate Chemistry 2017, 28, 1931. UCL RPS link doi: 10.1021/acs.bioconjchem.7b00253

59. A. Dunbabin, F. Subrizi, J. M. Ward, T. D. Sheppard, H. C. Hailes, Furfurylamines from biomass: transaminase catalysed upgrading of furfurals, Green Chemistry 2017, 19, 397. doi: 10.1039/C6GC02241C pdf Open Access

This article was featured in the inside back cover of Green Chemistry with a design by Alice and Fabiana incorporating a photo taken by Alice's dad.

58. L. Benhamou, D. W. Walker, D. -K. Bucar, A. E. Aliev, T. D. Sheppard, Synthesis of substituted benzooxaborinin-1-ols via palladium- catalysed cyclisation of alkenyl- and alkynyl-boronic acids, Organic & Biomolecular Chemistry 2016, 14, 8039. doi: 10.1039/C6OB01419D. pdf

57. R. M. Lanigan, V. Karaluka, M. Sabatini, P. Starkov, M. Badland, L. Boulton, T. D. Sheppard, Direct Amidation of Unprotected Amino Acids using B(OCH2CF3)3, Chemical Communications 2016, 52, 8846. doi: 10.1039/C6CC05147B. pdf Open Access

This article was highlighted in Synfacts and in an ACS Cutting Edge Chemistry article.

56. M. N. Pennell, M. P. Kyle, S. M. Gibson, L. Male, P. G. Turner, R. S. Grainger, T. D. Sheppard, Intercepting the Gold-Catalysed Meyer–Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols, Advanced Synthesis & Catalysis 2016, 358, 1519. doi: 10.1002/adsc.201600101. Open Access

55. F. Subrizi, M. Cardenas-Fernandez, G. J. Lye, J. M. Ward, P. A. Dalby, T. D. Sheppard, H. C. Hailes, Transketolase catalysed upgrading of L-arabinose: the one-step stereoselective synthesis of L-gluco-heptulose, Green Chemistry 2016 18, 3158. doi: 10.1039/C5GC02660A. pdf Open Access

54. S. Higson, F. Subrizi, T. D. Sheppard, H. C. Hailes, Chemical Cascades in Water for the Synthesis of Functionalized Aromatics from Furfurals, Green Chemistry 2016 18, 1855. doi: 10.1039/C5GC02935J. pdf Open Access

This article was featured in the inside back cover of Green Chemistry with a design by Sally and Fabiana incorporating a photo taken by Tom of the Tvindefossen waterfall in Norway.

53. P. M. Murray, F. Bellany, L. Benhamou, D. -K, Bucar, A. B. Tabor, T. D. Sheppard, The application of design of experiments (DoE) reaction optimisation and solvent selection in the development of new synthetic chemistry, Organic & Biomolecular Chemistry 2016 14, 2373. doi: 10.1039/C5OB01892G. pdf Open Access

This article was featured on the front cover of OBC with a design incorporating a photo taken by Tom of the ridge running between Herzogstand and Heimgarten on the edge of the Bavarian alps.

52. E. Barreiro, A. Sanz-Vidal, E. Tan, S. -H. Lau, T. D. Sheppard, S. Díez-González, HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols, European Journal of Organic Chemistry 2015, 34, 7544. doi: 10.1002/ejoc.201501249. Open Access

51. F. Rota, L. Benhamou, T. D. Sheppard, Asymmetric Synthesis of Secondary Alcohols and 1,2-Disubstituted Epoxides via Organocatalytic Sulfenylation, Synlett (Special Issue Celebrating the 70th Birthday of Professor Steven Ley CBE FRS) 2016, 37, 33. doi: 10.1055/s-0035-1560769. pdf

50. R. W. Foster, C. J. Tame, D -K. Bucar, H. C. Hailes, T. D. Sheppard, The Sustainable Synthesis of Chiral Tetrahydrofurans via the Selective Dehydration of Pentoses, Chemistry - A European Journal 2015, 21, 15947. doi: 10.1002/chem.201503510. Open Access

49. V. Karaluka, R. M. Lanigan, P. M. Murray, M. Badland, T. D. Sheppard, B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether, Organic & Biomolecular Chemistry 2015, 13, 10888. doi: 10.1039/c5ob01801c. pdf Open Access

48. S. M. Gibson, R. M. Lanigan, L. Benamou, A. E. Aliev, T. D. Sheppard, A Lactate-Derived Chiral Aldehyde for Determining the Enantiopurity of Enantioenriched Primary Amines, Organic & Biomolecular Chemistry 2015, 13, 9050. doi: 10.1039/c5ob01398d. pdf Open Access

47. A. Chatzidaki, J. M. D'Oyley, J. K. Gill-Thind, T. D. Sheppard, N. S. Millar, The influence of allosteric modulators and transmembrane mutations on desensitisation and activation of α7 nicotinic acetylcholine receptors, Neuropharmacology 2015 97, 75. doi: 10.1016/j.neuropharm.2015.05.006. Open Access

46. R. W. Foster, L. Benhamou, M. J. Porter, D. -K. Bucar, H. C. Hailes, C. J. Tame, T. D. Sheppard, Irreversible endo-Selective Diels-Alder Reactions of Substituted Alkoxyfurans: a General Synthesis of endo-Cantharimides, Chemistry - A European Journal 2015 21, 6107. doi: 10.1002/chem.201406286. Open Access

45. J. K. Gill-Thind, P. Dhankher, J. M. D'Oyley, T. D. Sheppard, N. S. Millar, Structurally similar allosteric modulators of α7 nicotinic acetylcholine receptors exhibit five distinct pharmacological effects, Journal of Biological Chemistry 2015, 290, 3552. doi: 10.1074/jbc.M114.619221.

44. S. A. Samchez-Vasquez, T. D. Sheppard, J. R. G Evans, H. C. Hailes, The selective conversion of D-limonene to p,α-dimethylstyrene, RSC Advances 2014 4, 61652. doi: 10.1039/c4ra11558a.

43. P. Dhankher, L. Benhamou, T. D. Sheppard, Rapid Assembly of Functionalised Spirocyclic Indolines by Palladium-Catalysed Dearomatising Diallylation of Indoles with Allyl Acetate, Chemistry - A European Journal 2014 20, 13375. doi: 10.1002/chem.201403940. UCL RPS link Open Access

42. J. M. D'Oyley, A. E. Aliev, T. D. Sheppard, Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Non-Catalyzed Reactions, Angewandte Chemie International Edition 2014 53, 10747. doi: 10.1002/anie.201405348. UCL RPS link Open Access

41. M. N. Pennell, R. W. Foster, P. G. Turner, H. C. Hailes, C. J. Tame, T. D. Sheppard, Gold catalysed synthesis of 3-alkoxyfurans at room temperature, Chemical Communications 2014 50, 1302. doi: 10.1055/s-0033-1340302. UCL RPS link Open Access

40. P. Dhankher, T. D. Sheppard, A Convenient Synthesis of Tri- and Tetramethylbenzaldehydes from Readily Available Phenols, Synlett 2014, 381. doi: 10.1055/s-0033-1340302. UCL RPS linkpdf

39. R. W. Foster, C. J. Tame, H. C. Hailes, T. D. Sheppard, Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium-Catalyzed Alkyne Cyclotrimerizations, Advanced Synthesis & Catalysis 2013, 355, 2353. doi: 10.1002/adsc.201300055. UCL RPS link Open Access

38. A. E. Aliev, M. Kulke, H. S. Khaneja, V. Chudasama, T. D. Sheppard, R. M. Lanigan, Motional timescale predictions by molecular dynamics simulations: Case study using proline and hydroxyproline sidechain dynamics, Proteins 2014, 82, 195. doi: 10.1002/prot.24350 UCL RPS link Open Access.

37. R. M. Lanigan, P. Starkov and T. D. Sheppard, Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH2CF3)3, The Journal of Organic Chemistry 2013, 78, 4512. doi:10.1021/jo400509n. UCL RPS link Open Access

Highlighted on www.organic-chemistry.org.

This article regularly appears in the most read articles (past 12 months) in JOC.

36. P. Starkov, F. Rota, J. M. D'Oyley and T. D. Sheppard, Catalytic Electrophilic Halogenation of Silyl-Protected and Terminal Alkynes: Trapping Gold(I) Acetylides vs. a Brønsted Acid-Promoted Reaction, Advanced Synthesis & Catalysis 2012, 354, 3217. doi:10.1002/adsc.201200491. UCL RPS link

35. M. N. Pennell, P. G. Turner and T. D. Sheppard, Gold and Silver Catalyzed Reactions of Propargylic Alcohols in the Presence of Protic Additives, Chemistry - A European Journal 2012, 18, 4748. doi:10.1002/chem.201102830. UCL RPS link

34. J. K. Gill, P. Dhankher, T. D. Sheppard, E. Sher, N. S Millar, A Series of α7 Nicotinic Acetylcholine Receptor Allosteric Modulators with Close Chemical Similarity but Diverse Pharmacological Properties, Molecular Pharmacology, 2012, 81, 710. doi:10.1124/mol.111.076026 UCL RPS link Open Access

33. M. Bachman, S. E. Mann, T. D. Sheppard, Rapid Synthesis of Highly Functionalised Alpha-Amino Amides and Medium Ring Lactones using Multicomponent Reactions of Amino Alcohols and Isocyanides , Organic and Biomolecular Chemistry, 2012, 10, 162. doi:10.1039/C1OB06534C. UCL RPS link pdf.

32. S. E. Mann, A. E. Aliev, G. J. Tizzard, T. D. Sheppard, Sulfur-Directed Olefin Oxidations: Observation of Divergent Reaction Mechanisms in the Palladium-Mediated Acetoxylation of Unsaturated Thioacetals, Organometallics, 2011, 30, 1772. doi:10.1021/om2000585. UCL RPS link

31. M. N. Pennell, M. G. Unthank, P. Turner, T. D. Sheppard, A General procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rerrangement of propargylic alcohols at room temperature, The Journal of Organic Chemistry, 2011, 76, 1479. doi:10.1021/jo102263t. UCL RPS link

Highlighted on www.organic-chemistry.org.

30. P. Starkov, T. D. Sheppard, Borate esters as convenient reagents for direct amidation of carboxylic acids and transamidation of primary amides, Organic and Biomolecular Chemistry, 2011, 9, 1320. doi:10.1039/C0OB1069C. UCL RPS link

29. C. Körner, Eun-Ang Raiber, Samuel E. M. Keegan, Daniel C. Nicolau, T. D. Sheppard, Alethea B. Tabor, An expedient synthesis of orthogonally protected lysinoalanine from Aloc-protected Garner's aldehyde, Tetrahedron Letters, 2010, 51, 6381. doi:10.1016/j.tetlet.2010.09.119. UCL RPS link

28. C. Körner, P. Starkov, T. D. Sheppard, An Alternative approach to aldol reactions: Gold-catalyzed formation of boron enolates from alkynes, Journal of the American Chemical Society, 2010, 132, 5968. doi:10.1021/ja102129c. UCL RPS link

Reviews, Conference Reports, etc

27. S. Ishida, T. D. Sheppard, T. Nishikata, Site selectivities in fluorination, Tetrahedron Letters 2018, 59, 789. doi: 10.1016/j.tetlet.2018.01.044

26. M. Cardenas-Fernandez, M. Bawn, C. Bennett, B. Penumathsa, F. Subrizi, N. Suhaili, D. Ward, S. Bourdin, P. A Dalby, H. C. Hailes, P. Hewitson, S. Ignatova, C. Kontoravdi, D. J. Leak, N. Shah, T. D. Sheppard, J. M Ward and G. J Lye, An Integrated Biorefinery Concept for Conversion of Sugar Beet Pulp into Value-added Chemicals and Pharmaceuticals, Faraday Discussions, 2017, 202, 415. doi: 10.1039/C7FD00094D.

25. S. E. Mann, L. Benhamou, T. D. Sheppard, Palladium(II)-Catalysed Oxidation of Alkenes, Synthesis, 2015, 47, 3079. doi: 10.1055/s-0035-1560465. pdf

24. T. D. Sheppard, Tris(2,2,2-trifluoroethoxy)boron, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2014. doi: 10.1002/047084289X.rn01754.

23. R. M. Lanigan, T. D. Sheppard, Recent Developments in Amide Synthesis: Direct Amidation of Carboxylic Acids and Transamidation Reactions, European Journal of Organic Chemistry 2013, 7453. doi: 10.1002/ejoc.201300573. UCL RPS link

22. T. D. Sheppard and T. N. Snaddon, Highlights from the 47th EUCHEM Conference on Stereochemistry, Bürgenstock, Switzerland, May 2012, Chemical Communications 2012, 48, 11597. doi:10.1039/C2CC90366K pdf. UCL RPS link

21. T. D. Sheppard, Complexity-generating hydration reactions via gold-catalyzed addition of boronic acids to alkynes, Pure and Applied Chemistry 2012, 84, 2431. doi:10.1351/PAC-CON-12-01-08. UCL RPS link

20. T. D. Sheppard, Strategies for the Synthesis of 2,3-Dihydrobenzofurans, Journal of Chemical Research, 2011, 377. doi:10.3184/174751911X13096980701749. UCL RPS link

19. T. D. Sheppard, Alternative Approaches to Enolate Chemistry, Synlett, 2011, 1340. doi:10.1055/s-0030-1260570. UCL RPS link

18. T. D. Sheppard, Metal-catalysed Halogen Exchange Reactions of Aryl Halides, Organic and Biomolecular Chemistry 2009, 7, 1043. doi:10.1039/b818155a. UCL RPS link pdf

Postdoctoral Research (with Professor W. B. Motherwell)

17. S. Ishikawa, T. D. Sheppard, J. M. D'Oyley, A. Kamimura, W. B. Motherwell, A Rapid Route to Aminocyclopropanes via Carbamatoorganozinc Carbenoids, Angewandte Chemie International Edition 2013, 52, 10060. doi: 10.1002/anie.201304720. UCL RPS link Open Access

16. R. W. Waller, L. J. Diorazio, B. A. Taylor, W. B. Motherwell, T. D. Sheppard, Isocyanide Based Multicomponent Reactions of Oxazolidines and Related Systems, Tetrahedron, 2010, 66, 6496. doi:10.1016/j.tet.2010.05.083. UCL RPS link

15. L. Jerome, T. D. Sheppard, A. E. Aliev, W. B. Motherwell, Intramolecular amidocyclopropanation reactions using diethoxymethyl-functionalised lactams as organozinc carbenoid precursors, Tetrahedron Letters, 2009, 50, 3709. doi:10.1016/j.tetlet.2009.03.224. UCL RPS link

14. W. B. Motherwell, G Bégis, D. Cladingboel, L. Jerome and T. D. Sheppard, Asymmetric Synthesis of Aminocyclopropanes and N-cyclopropylamino alcohols via Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids, European Journal of Organic Chemistry, 2009, 1532. doi:10.1002/ejoc.200801033.

13. P. J. Gray, W. B. Motherwell, T. D. Sheppard and A. J. Whitehead, Observations on the Synthesis & Carbocyclisation Reactions of 6-oxohexa-2,3-dienoates, Synlett, special issue commemorating the 70th birthday of Professor Sir Jack Baldwin, 2008, 2097. doi:10.1055/s-2008-1078028.

12. S. S. Ramos, W. B. Motherwell, P. Almeida, L. Santos, T. D. Sheppard and M. C. Costa, Functionalisation of terpenoids at C-4 using organopalladium dimers - unusual participation of an adjacent alkene during the oxidation of the palladium-carbon bond, leading to cyclopropane formation, Tetrahedron 2007, 63, 12608. doi:10.1016/j.tet.2007.10.016. UCL RPS link

11. W. B. Motherwell, G Bégis, D. Cladingboel, L. Jerome and T. D. Sheppard, Observations on the direct amidocyclopropanation of alkenes using organozinc carbenoids, Tetrahedron 2007, 63, 6462. doi:10.1016/j.tet.2007.03.027. UCL RPS link

10. L. J. Diorazio, W. B. Motherwell, T. D. Sheppard and R. W. Waller, Observations on the reaction of N-alkyloxazolidines, isocyanides and carboxylic acids: A novel three-component reaction leading to N-acyloxyethylamino acid amides, Synlett 2006, 2281. doi:10.1055/s-2006-950413.

9. G Bégis, T. D. Sheppard, D. Cladingboel, W. B. Motherwell, and D. A. Tocher, Synthesis of enantiopure aminocyclopropanes by diastereoselective addition of a chiral amino substituted organozinc carbenoid to alkenes, Synthesis, special issue commemorating the 60th birthday of Professor SV Ley, 2005, 3186. doi:10.1055/s-2005-918469.

PhD (with Professor S. V. Ley)

8. S. V. Ley, T. D. Sheppard, R. M. Myers and M. K. Chorgade, Chiral glycolate equivalents for the asymmetric synthesis of α-hydroxycarbonyl compounds, Bulletin of the Chemical Society of Japan 2007, 80, 1451. doi:10.1246/bcsj.80.1451.

7. S. V. Ley, D. J. Dixon, R. T. Guy, F. Rodriguez and T. D. Sheppard, Michael, Michael-aldol and Michael-Michael reactions of enolate equivalents of butane-2,3-diacetal protected glycolic acid derivatives, Organic and Biomolecular Chemistry, 2005, 3, 4095. doi:10.1039/b512410g.

6. D. J. Dixon, S. V. Ley, S. Lohmann and T. D. Sheppard, Synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab erimacrus isenbeckii using butane-2,3-diacetal desymmetrised glycolic acid building blocks, Synlett 2005, 481. doi:10.1055/s-2005-862361.

5. S. V. Ley, D. J. Dixon, R. T. Guy, M. A. Palomero, A. Polara, F. Rodriguez and T. D. Sheppard, Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides, Organic and Biomolecular Chemistry 2004, 2, 3618. doi:10.1039/b412790k.

4. S. V. Ley, E. Diez, D. J. Dixon, R. T. Guy, P. Michel, G. L. Nattrass and T. D. Sheppard, Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives, Organic and Biomolecular Chemistry 2004, 2, 3608. doi:10.1039/b412788a.

3. D. J. Dixon, S. V. Ley, A. Polara and T. D. Sheppard, Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrised glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters, Organic Letters 2001, 3, 3749. doi:10.1021/ol016707n.

Industrial Research (GlaxoWellcome)

2. M. Ladlow, C. H. Legge, T. Neudeck, A. Pipe, T. D. Sheppard and L. L. Yang, Wavelength dependent photo-controlled differential release of compounds from solid phase resin, Chemical Communications 2003, 2048. doi:10.1039/b304477g.

1. M. S. Congreve, M. Ladlow, P. Marshall, N. Parr, J. J. Scicinski, T. D. Sheppard, E. Vickerstaffe and R. A. E. Carr, Reporter resins for solid-phase chemistry, Organic Letters 2001, 3, 507. doi:10.1021/ol006751n.

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