Prof. Richard F. W. Jackson
Professor of Synthetic Organic Chemistry
Prof. Jackson obtained his BA in Chemistry from the University of Cambridge in 1981. After his PhD (Cambridge 1984) he became a Postdoctoral Research Fellow at the ETH in Zürich, Switzerland. In 1985 he was appointed to a lectureship at the University of Newcastle, where he was promoted to Reader in 1994 and to Professor in Synthetic Organic Chemistry in 1996. In 2001 he was appointed to a Chair in Synthesis at the University of Sheffield. He served as Head of the Department of Chemistry from 2003-2007 and has returned to this role for a further term (2011-2014).
Organic Synthesis, organozinc chemistry, combinatorial and asymmetric catalysis
- New Routes to Lipophilic Amino Acids: Synthesis of Alkynyl and Fluoro-Containing Alanine Derivatives, Claudia Wuttke, Rebecca Ford, Matthew Lilley, Urszula Grabowska, Daniel Wiktelius and Richard F. W. Jackson, Synlett 2012, 243-246.
- Evidence for the Role of Tetramethylethylenediamine in Aqueous Negishi Cross-Coupling: Synthesis of Nonproteinogenic Phenylalanine Derivatives on Water, A. J. Ross, F. Dreiocker, M. Schaefer, J. Oomens, A. J. H. M. Meijer, B. T. Pickup and R. F. W. Jackson, J. Org. Chem. 2011, 76, 1727-1734..
- In Situ trapping of Boc-2-pyrrolidinylmethylzinc Iodide with Aryl Iodides: Direct Synthesis of 2-Benzylpyrrolidines, A. R. Massah, A. J. Ross and R. F. W. Jackson, J. Org. Chem. 2010, 75, 8275-8278.
- Structure Elucidation of Dimethylformamide-Solvated Alkylzinc Cations in the Gas Phase, F. Dreiocker, J. Oomens, A. J. H. M. Meijer, B. T. Pickup, R. F. W. Jackson and M. Schafer, J. Org. Chem. 2010, 75, 1203-1213.
- Much Improved Conditions for the Negishi Cross-Coupling of Iodoalanine Derived Zinc Reagents with Aryl Halides, A. J. Ross, H. L. Lang and R. F. W. Jackson, J. Org. Chem. 2010, 75, 245-248.
- Application of Negishi Cross-Coupling to the Synthesis of the Cyclic Tripeptides OF4949-III and K-13, L. Nolasco, M. P. Gonzalez, L. Caggiano and R. F. W. Jackson, J. Org. Chem. 2009, 74, 8280-8289.
- Kinetic Studies on the Stability and Reactivity of beta-Amino Alkylzinc Iodides Derived from Amino Acids, I. Rilatt and R. F. W. Jackson, J. Org. Chem. 2008, 73, 8694-8704.
- Ionisation of the Zinc-Iodine Bond of Alkylzinc Iodides in Dimethylformamide from Theory and Experiment, L. Caggiano, R. F. W. Jackson, A. J. H. M. Meijer, B. T. Pickup and K. A. Wilkinson, Chem-Eur J 2008, 14, 8798-8802.
- Development and applications of amino acid derived organometallics, I. Rilatt, L. Caggiano and R. F. W. Jackson, Synlett 2005, 2701-2719.
- Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides, C. Drago, L. Caggiano and R. F. W. Jackson, Angew Chem Int Edit 2005, 44, 7221-7223.
I carried out research for my PhD under the supervision of the late Professor Ralph Raphael. I developed a new route to dihydrofuranones, and completed a synthetic approach to the Pseudomonic acids. With this training in target synthesis, I spent one year at the ETH, Zürich, working with Professor Dieter Seebach on the synthesis of a derivative of the macrodiolide Elaiophylin.
I returned to the UK in 1985 to take up a lectureship in Newcastle. Our initial work was in nucleophilic epoxidation, and epoxide anion chemistry, but we also initiated a programme in the area of unnatural amino acid synthesis. We found that organozinc derivatives of amino acids could be prepared, were surprisingly stable, and provided an easy route to a large variety of useful compounds. This latter area blossomed, and resulted in various awards, from Pfizer, Zeneca and the Hickinbottom Fellowship of the Royal Society of Chemistry.
More recently, we have extended our research to the area of asymmetric catalysis, and discovered a simple method for the asymmetric epoxidation of enones, and a highly efficient method for the asymmetric oxidation of alkyl aryl sulfides to the corresponding sulfoxides. We are also interested in solid phase chemistry, and the application of combinatorial techniques to the discovery of new catalysts.
Undergraduate Courses Taught
- Organic Chemistry 2 (Year 1)
This segment provides an introduction into the structure and reactivity of carbonyl compounds with particular emphasis on aldehydes and ketones.
- Strategy in Synthesis 1 (Year 3)
This course introduces the ideas of retrosynthetic analysis, providing a basis for the design of synthetic routes, and to reinforce key aspects of basic organic chemistry, especially drawing molecules, pKa values and mechanism.
- Metals in Organic Synthesis (Year 4)
This course describes the use of organometallic reagents in synthesis. In particular, the use of both stoichiometric organometallics and transition metal catalysts is illustrated.
Tutorial & Workshop Support
- Second Year Organic Chemistry Tutorials
- Third Year Workshops.
- Fourth Year Research Project.
- Lilley M, Mambwe B, Jackson RF & Muimo R (2014) 4-Phosphothiophen-2-yl alanine: a new 5-membered analogue of phosphotyrosine.. Chem Commun (Camb), 50(66), 9343-9345.
- Wuttke C, Ford R, Lilley M, Grabowska U, Wiktelius D & Jackson RFW (2012) New routes to lipophilic amino acids: Synthesis of alkynyl and fluoro-containing alanine derivatives. Synlett(2), 243-246.
- Massah AR, Dreiocker F, Jackson RFW, Pickup BT, Oomens J, Meijer AJHM & Schafer M (2011) Gas-phase study of new organozinc reagents by IRMPD-spectroscopy, computational modelling and tandem-MS. PHYS CHEM CHEM PHYS, 13(29), 13255-13267.
- Massah AR, Dreiocker F, Jackson RF, Pickup BT, Oomens J, Meijer AJ & Schäfer M (2011) Gas-phase study of new organozinc reagents by IRMPD-spectroscopy, computational modelling and tandem-MS.. Phys Chem Chem Phys, 13(29), 13255-13267.
- Ross AJ, Dreiocker F, Schäfer M, Oomens J, Meijer AJ, Pickup BT & Jackson RF (2011) Evidence for the role of tetramethylethylenediamine in aqueous Negishi cross-coupling: synthesis of nonproteinogenic phenylalanine derivatives on water.. J Org Chem, 76(6), 1727-1734.
- Massah AR, Ross AJ & Jackson RF (2010) In situ trapping of Boc-2-pyrrolidinylmethylzinc iodide with aryl iodides: direct synthesis of 2-benzylpyrrolidines.. J Org Chem, 75(23), 8275-8278.
- Dreiocker F, Oomens J, Meijer AJ, Pickup BT, Jackson RF & Schäfer M (2010) Structure elucidation of dimethylformamide-solvated alkylzinc cations in the gas phase.. J Org Chem, 75(4), 1203-1213.
- Ross AJ, Lang HL & Jackson RF (2010) Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides.. J Org Chem, 75(1), 245-248.
- Goddard CML, Massah AR & Jackson RFW (2010) Improved synthesis of phenylethylamine derivatives by Negishi cross-coupling reactions. Tetrahedron, 66(47), 9175-9181.
- Nolasco L, Perez Gonzalez M, Caggiano L & Jackson RF (2009) Application of Negishi cross-coupling to the synthesis of the cyclic tripeptides OF4949-III and K-13.. J Org Chem, 74(21), 8280-8289.
- Bartrum HE & Jackson RFW (2009) An approach to the synthesis of anti-β2,3-amino acids: Application of β-trifluoroacetamidoorganozinc reagents. Synlett(14), 2257-2260.
- Heravi MRP, Loghmani-Khouzani H, Sadeghi MM, Zendehdel M, Jackson RF & Adams H (2009) Crystal structure of 2-(4-methoxybenzylthio)-1-phenylethanone. X-ray Structure Analysis Online, 25(4), 43-44.
- Drago C, Walker E-J, Caggiano L, Jackson RFW, Rawls K & Ellman JA (2009) Enantioselective oxidation of an alkyl aryl sulfide: Synthesis of (S)-(-)-methyl p-Bromophenyl sulfoxide. Organic Syntheses, 86, 121-129.
- Rilatt I & Jackson RF (2008) Kinetic studies on the stability and reactivity of beta-amino alkylzinc iodides derived from amino acids.. J Org Chem, 73(22), 8694-8704.
- Jamookeeah CE, Beadle CD, Jackson RF & Harrity JP (2008) Investigation of a flexible enantiospecific approach to aziridines.. J Org Chem, 73(3), 1128-1130.
- Caggiano L, Jackson RF, Meijer AJ, Pickup BT & Wilkinson KA (2008) Ionisation of the zinc--iodine bond of alkylzinc iodides in dimethylformamide from theory and experiment.. Chemistry, 14(29), 8798-8802.
- Oswald CL, Carrillo-Márquez T, Caggiano L & Jackson RFW (2008) Negishi cross-coupling reactions of α-amino acid-derived organozinc reagents and aromatic bromides. Tetrahedron, 64(4), 681-687.
- Bartrum HE, Adams H, Caggiano L & Jackson RFW (2008) Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions. Tetrahedron, 64(17), 3701-3712.
- Loghmani-Khouzani H, Poorheravi MR, Sadeghi MMM, Caggiano L & Jackson RFW (2008) α-Fluorination of β-ketosulfones by Selectfluor™ F-TEDA-BF4. Tetrahedron, 64(30-31), 7419-7425.
- Poorheravi MR, Loghmani-Khouzani H, Sadeghi MMM, Zendehdel M, Jackson RFW & Adams H (2008) Crystal structure of 2-hydroxy-2-(2-methyl-1H-indol-3-yl)- 2h-indene-1,3-dione. Analytical Sciences: X-ray Structure Analysis Online, 24(3).
- Evans LA, Adams H, Barber CG, Caggiano L & Jackson RF (2007) Stereoselective synthesis of 2,3-difunctionalised thioesters using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes.. Org Biomol Chem, 5(19), 3156-3163.
- Poorheravi MR, Loghmani-Khouzani H, Sadeghi MM, Zendehdel M, Jackson RF & Adams H (2007) Crystal structure of 2,2-bis(6-hydroxy-biphenyl-3-yl)-1H-indene-1,3(2H)-dione. Analytical Sciences: X-ray Structure Analysis Online, 23(11).
- Moreno E, Nolasco LA, Caggiano L & Jackson RF (2006) Synthesis of orthogonally protected biaryl amino acid derivatives.. Org Biomol Chem, 4(19), 3639-3647.
- Hinch M, Jacques O, Drago C, Caggiano L, Jackson RFW, Dexter C, Anson MS & Macdonald SJF (2006) Effective asymmetric oxidation of enones and alkyl aryl sulfides. Journal of Molecular Catalysis A: Chemical, 251(1-2), 123-128.
- Mohammadpoor-Baltork I, Hill M, Caggiano L & Jackson RFW (2006) Oxidative kinetic resolution of alkyl aryl sulfoxides. Synlett(20), 3540-3544.
- Carrillo-Marquez T, Caggiano L, Jackson RF, Grabowska U, Rae A & Tozer MJ (2005) New routes to beta-cycloalkylalanine derivatives using serine-derived organozinc reagents.. Org Biomol Chem, 3(22), 4117-4123.
- Drago C, Caggiano L & Jackson RF (2005) Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides.. Angew Chem Int Ed Engl, 44(44), 7221-7223.
- Rilatt I, Caggiano L & Jackson RFW (2005) Development and applications of amino acid derived organometallics. Synlett(18), 2701-2719.
- Jackson RFW & Perez-Gonzalez M (2005) Synthesis of N-(tert-Butoxycarbonyl)-β-iodoalanine methyl ester: A useful building block in the synthesis of nonnatural α-amino acids via palladium catalyzed cross coupling reactions. Organic Syntheses, 81.
- Jackson RF, Rilatt I & Murray PJ (2004) Direct synthesis of unprotected phenols using palladium-catalysed cross coupling reactions of functionalised organozinc reagents.. Org Biomol Chem, 2(1), 110-113.
- Tabanella S, Valancogne I & Jackson RF (2003) Preparation of enantiomerically pure pyridyl amino acids from serine.. Org Biomol Chem, 1(23), 4254-4261.
- Jackson RF, Dunn SF, McCamley A & Clegg W (2003) Synthesis and crystal structures of 2-substituted-2-phenylsulfonyloxiranes: evidence for a generalised anomeric effect in 2-phenylsulfonyloxiranes.. Org Biomol Chem, 1(14), 2527-2530.
- Jackson RF, Rilatt I & Murray PJ (2003) The rate of elimination of a beta-amino zinc reagent is reduced by using a better leaving group.. Chem Commun (Camb)(11), 1242-1243.
- Rodríguez A, Miller DD & Jackson RF (2003) Combined application of organozinc chemistry and one-pot hydroboration-Suzuki coupling to the synthesis of amino acids.. Org Biomol Chem, 1(6), 973-977.
- Oates LJ, Jackson RFW & Block MH (2003) Cross coupling reactions of organozinc iodides with solid-supported electrophiles: synthesis of 4-substituted benzoic and 3-substituted (E)- and (Z)-propenoic acids and amides. ORG BIOMOL CHEM, 1(1), 140-144.
- Clegg W, Heath SL, Jackson RFW & Palmer NJ (2003) [3R-(3β4β,5β)]-3-(Acetylamino)-3,4-dihydro-4-hydroxy-5- (hydroxymethyl)-furan-2(5H)-one monohydrate. Acta Crystallographica Section E: Structure Reports Online, 59(7).
- Pelotier B, Anson MS, Campbell IB, Macdonald SJF, Priem G & Jackson RFW (2002) Enantioselective sulfide oxidation with H2O2: A solid phase and array approach for the optimisation of chiral Schiff base-vanadium catalysts. Synlett(7), 1055-1060.
- MacCulloch AC, Yolka S & Jackson RFW (2002) Asymmetric Michael reactions using tartrate-based magnesium catalysts. Synlett(10), 1700-1702.
- Ambroise L, Dumez E, Szeki A & Jackson RFW (2002) Stereocontrolled synthesis of anti-α-hydroxy-β-amino and anti-α,β-diamino acid derivatives by epoxidation of 1-arylthio-1-nitroalkenes. Synthesis(15), 2296-2308.
- Ambroise L, Dumez E, Szeki A & Jackson RFW (2002) Stereocontrolled synthesis of anti-alpha-hydroxy-beta-amino and anti-alpha,beta-diamino acid derivatives by epoxidation of 1-arylthio-l-nitroalkenes. SYNTHESIS-STUTTGART(15), 2296-2308.
- MacCulloch AC, Yolka S & Jackson RFW (2002) Asymmetric Michael reactions using tartrate-based magnesium catalysts. SYNLETT(10), 1700-1702.
- Pelotier B, Anson MS, Campbell IB, Macdonald SJF, Priem G & Jackson RFW (2002) Enantioselective sulfide oxidation with H2O2: A solid phase and array approach for the optimisation of chiral Schiff base-vanadium catalysts. SYNLETT(7), 1055-1060.
- Deboves HJC, Hunter C & Jackson RFW (2002) Synthesis of 2-substituted indolines using sequential Pd-catalyzed processes. Journal of the Chemical Society. Perkin Transactions 1(6), 733-736.
- Dumez E, Snaith JS, Jackson RFW, McElroy AB, Overington J, Wythes MJ, Withka JM & McLellan TJ (2002) Synthesis of macrocyclic, potential inhibitors using a generic scaffold. Journal of Organic Chemistry, 67(14), 4882-4892.
- Wilson I & Jackson RFW (2002) Palladium(O) catalysed and copper(I) promoted reactions of the secondary zinc reagent derived from L-threonine. Journal of the Chemical Society. Perkin Transactions 1(24), 2845-2850.
- Green SD, Monti C, Jackson RFW, Anson MS & Macdonald SJF (2001) Discovery of new solid phase sulfur oxidation catalysts using library screening. CHEM COMMUN(24), 2594-2595.
- Dumez E, Szeki A & Jackson RFW (2001) Stereoselective synthesis of differentially protected anti-alpha,beta-diamino acid derivatives using arylthionitrooxiranes. SYNLETT(8), 1214-1216.
- Deboves HJC, Montalbetti CAGN & Jackson RFW (2001) Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: Application to polymethoxylated phenylalanines and 4-oxoamino acids. Journal of the Chemical Society. Perkin Transactions 1(16), 1876-1884.
- Hunter C, Jackson RFW & Rami HK (2001) Improved catalytic procedures for the copper(I)-promoted reactions of β-amido zinc reagents. Journal of the Chemical Society. Perkin Transactions 1(12), 1349-1352.
- Jacques O, Richards SJ & Jackson RFW (2001) Catalytic asymmetric epoxidation of aliphatic enones using tartrate-derived magnesium alkoxides. Chemical Communications(24), 2712-2713.