The University of Sheffield
Department of Chemistry

Richard JacksonProf. Richard F. W. Jackson

Head of Department

Professor of Synthetic Organic Chemistry

Room: C86

Tel: +44-(0)114-22-29464 (direct)/+44-(0)114-22-29319 (Secretary)

Fax: +44-(0)114-22-29436

Email: ch-hod@sheffield.ac.uk  - Personal email: r.f.w.jackson@sheffield.ac.uk


 

General  Research Teaching

Biographical Sketch

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 four year term (2011-2015).

Research Keywords

Organic Synthesis, organozinc chemistry, combinatorial and asymmetric catalysis

Teaching Keywords

Organic Chemistry

Selected Publications:

  • 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.

Research Interests

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.

ZincReagents

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.

Teaching Section

Organic Chemistry

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.

Laboratory Teaching

  • Fourth Year Research Project.