Clayden, Jonathan - The University of Manchester

个人简介

Jonathan Clayden obtained his first degree and PhD from the University of Cambridge, where he worked with Dr Stuart Warren on asymmetric synthesis using phosphine oxide chemistry. He spent 18 months as a Royal Society Western European Research Fellow in the laboratories of Prof. Marc Julia in Paris, before moving in 1994 to Manchester as a Lecturer. In 2001 he was promoted to a personal chair in Organic Chemistry. He has been awarded the Royal Society of Chemistry's Meldola and Corday-Morgan Medals and Hickinbottom Fellowship, and he has received research prizes from GlaxoWellcome, AstraZeneca, Pfizer and Novartis. He is author of the undergraduate textbook "Organic Chemistry" (Clayden, Greeves, Warren and Wothers, pub OUP 2001) and of "Organolithiums, Selectivity for Synthesis" (pub Pergamon Press 2002).

研究领域

We make new molecules with interesting properties - biological activity or unusual stereochemical features, for example - with control over their stereochemistry. Current synthetic targets include the kainoid family of amino acids, many of which have never been synthesised, and potential anti-viral compounds including carbocyclic sugar analogues. The kainoids are important tools in the battle against Alzheimer's disease, and we collaborate with several pharmaceutical companies (mainly through CASE awards). We aim to use reactions we have discovered and developed within the group, such as our dearomatising cyclisation and rearrangement reactions, alongside the full battery of organic synthetic methods, to synthesise molecules efficiently. We also aim to use the new concepts we have introduced to stereoselective synthesis - conformational interlocking in remote stereocontrol, "action-at-a-distance" auxiliaries, deuterium as a protecting group, etc. - to expand the prospects for reliable and predictable stereocontrolled reactions. We try to understand how the molecules work - particularly with regard to the relationship between conformation, configuration and reactivity - so that we can design new molecules which work for us. Among these new molecules are ligands based on rotationally restricted functional groups, which we use to catalyse new enantioselective reactions. We are also developing conformationally switchable peptide-like molecules for use as artificial transmembrane receptors.

近期论文

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Liam Byrne, Jordi Sol, Thomas Boddaert, Tommaso Marcelli, Ralph W. Adams, Gareth A. Morris, and Jonathan Clayden. Foldamer-Mediated Remote Stereocontrol: >1,60 Asymmetric Induction. Angewandte Chemie (International Edition). 2014; 53(1): 151-155. eScholarID:218724 | DOI:10.1002/anie.201308264 Adams R, Byrne L, Király P, Foroozandeh M, Paudel L, Nilsson M, Clayden J, Morris G. Diastereomeric ratio determination by high sensitivity band-selective pure shift NMR spectroscopy. Chemical communications (Cambridge, England). 2014 March; 50(19): 2512-4. eScholarID:231127 | PMID:24458213 | DOI:10.1039/c3cc49659g Adams R, Byrne L, Király P, Foroozandeh M, Paudel L, Nilsson M, Clayden J, Morris G. Diastereomeric ratio determination by high sensitivity band-selective pure shift NMR spectroscopy. Chemical communications (Cambridge, England). 2014 March; 50(19): 2512-4. eScholarID:231152 | PMID:24458213 | DOI:10.1039/c3cc49659g Berber H, Lameiras P, Denhez C, Antheaume C, Clayden J. Atropisomerism about Aryl-Csp(3) Bonds: The Electronic and Steric Influence of ortho-Substituents on Conformational Exchange in Cannabidiol and Linderatin Derivatives. The Journal of organic chemistry. 2014 July; 79(13): 6015-27. eScholarID:231118 | PMID:24919056 | DOI:10.1021/jo5006069 Berber H, Lameiras P, Denhez C, Antheaume C, Clayden J. Atropisomerism about Aryl-Csp(3) Bonds: The Electronic and Steric Influence of ortho-Substituents on Conformational Exchange in Cannabidiol and Linderatin Derivatives. The Journal of organic chemistry. 2014 July; 79(13): 6015-27. eScholarID:231141 | PMID:24919056 | DOI:10.1021/jo5006069 Byrne L, Solà J, Boddaert T, Marcelli T, Adams R, Morris G, Clayden J. Foldamer-mediated remote stereocontrol: >1,60 asymmetric induction. Angewandte Chemie (International ed. in English). 2014 January; 53(1): 151-5. eScholarID:231128 | PMID:24375739 | DOI:10.1002/anie.201308264 Byrne L, Solà J, Boddaert T, Marcelli T, Adams R, Morris G, Clayden J. Foldamer-mediated remote stereocontrol: >1,60 asymmetric induction. Angewandte Chemie (International ed. in English). 2014 January; 53(1): 151-5. eScholarID:231144 | PMID:24375739 | DOI:10.1002/anie.201308264 De Poli M, Byrne L, Brown R, SolÃ J, Castellanos A, Boddaert T, Wechsel R, Beadle J, Clayden J. Engineering the structure of an N-terminal Î²-turn to maximize screw-sense preference in achiral helical peptide chains. The Journal of organic chemistry. 2014 May; 79(10): 4659-75. eScholarID:231124 | PMID:24708302 | DOI:10.1021/jo500714b De Poli M, Byrne L, Brown R, Solà J, Castellanos A, Boddaert T, Wechsel R, Beadle J, Clayden J. Engineering the structure of an N-terminal β-turn to maximize screw-sense preference in achiral helical peptide chains. The Journal of organic chemistry. 2014 May; 79(10): 4659-75. eScholarID:231153 | PMID:24708302 | DOI:10.1021/jo500714b De Poli M, Clayden J. Thionoglycine as a multifunctional spectroscopic reporter of screw-sense preference in helical foldamers. Organic & biomolecular chemistry. 2014 February; 12(5): 836-43. eScholarID:231136 | PMID:24336870 | DOI:10.1039/c3ob42167h De Poli M, Clayden J. Thionoglycine as a multifunctional spectroscopic reporter of screw-sense preference in helical foldamers. Organic & biomolecular chemistry. 2014 February; 12(5): 836-43. eScholarID:231150 | PMID:24336870 | DOI:10.1039/c3ob42167h Le Bailly B, Clayden J. Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer. Chemical communications (Cambridge, England). 2014 July; 50(59): 7949-52. eScholarID:231121 | PMID:24918692 | DOI:10.1039/c4cc03261f Le Bailly B, Clayden J. Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer. Chemical communications (Cambridge, England). 2014 July; 50(59): 7949-52. eScholarID:231143 | PMID:24918692 | DOI:10.1039/c4cc03261f Mingat G, McDouall J, Clayden J. Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis. Chemical communications (Cambridge, England). 2014 June; 50(51): 6754-7. eScholarID:231123 | PMID:24831495 | DOI:10.1039/c4cc02596b Mingat G, MacLellan P, Laars M, Clayden J. Tertiary thiols from allylic thiocarbamates by tandem enantioselective [3,3]-sigmatropic rearrangement and stereospecific arylation. Organic letters. 2014 February; 16(4): 1252-5. eScholarID:231137 | PMID:24502387 | DOI:10.1021/ol5002522 Mingat G, McDouall J, Clayden J. Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis. Chemical communications (Cambridge, England). 2014 June; 50(51): 6754-7. eScholarID:231157 | PMID:24831495 | DOI:10.1039/c4cc02596b Mingat G, MacLellan P, Laars M, Clayden J. Tertiary thiols from allylic thiocarbamates by tandem enantioselective [3,3]-sigmatropic rearrangement and stereospecific arylation. Organic letters. 2014 February; 16(4): 1252-5. eScholarID:231155 | PMID:24502387 | DOI:10.1021/ol5002522 Pike S, Raftery J, Webb S, Clayden J. Conformational analysis of helical aminoisobutyric acid (Aib) oligomers bearing C-terminal ester Schellman motifs. Organic & biomolecular chemistry. 2014 June; 12(24): 4124-31. eScholarID:231120 | PMID:24831537 | DOI:10.1039/c4ob00268g Pike S, Raftery J, Webb S, Clayden J. Conformational analysis of helical aminoisobutyric acid (Aib) oligomers bearing C-terminal ester Schellman motifs. Organic & biomolecular chemistry. 2014 June; 12(24): 4124-31. eScholarID:231138 | PMID:24831537 | DOI:10.1039/c4ob00268g