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Prof Jim C. Anderson

Head of Organic Chemistry and Chemical Biology Section

Summary
  Jim Anderson is a Professor of Organic Chemistry and work in his laboratory covers a broad portfolio of projects that combine contemporary synthetic organic chemistry methodology with highly adventurous, blue sky research. The basic theme in all of these projects is inventing fundamentally different ways of creating new organic structures in a stereocontrolled and, if applicable, catalytic fashion. This encompasses the development of new reaction methodology which is showcased in the synthesis of biologically active natural and non-natural products. He has worked at UCL since 2009. Before that he was at the department of Chemistry at the University of Nottingham for 10 years (2003-9: Professor of Chemistry; 1999-2002: Reader and EPSRC advanced fellow in organic chemistry) and began his academic career at the department of Chemistry at the University of Sheffield (1998-9 Senior Lecturer and EPSRC advanced fellow in organic chemistry; 1993-8: Lecturer)
Summary of research group
 

The nitro-Mannich reaction. We have designed and executed a new reaction for preparing 1,2-diamines, an important structural motif of asymmetric ligands and many biologically active compounds. The nitro-Mannich reaction relies upon the stereoselective addition of a nitronate anion to an imine, followed by subsequent reduction to give a 1,2-diamine. We have developed asymmetric protocols that rely upon chiral copper Lewis acids and the asymmetric conjugate addition of nucleophiles to nitroalkenes to form chiral nitronates in situ. These have been used intramolecularly to synthesise a variety of nitrogen heterocycles stereoselectively. Work continues developing more complex variants and applying the methodology to the synthesis of biologically active molecules.

The alpha-functionalisation of ethers. Cyclic benzylic and alkyl ethers are structurally interesting and pharmaceutically valuable compounds. We are developing methods of accessing unsaturated oxonium ions from ethers by hydride transfer or redox neutral rearrangements. Suitable nucleophiles should add to the unsaturated oxonium ions forming alpha-functionalised products. Methods will be investigated to make the process stereoselective and it will be applied to the synthesis of biologically active molecules.

The development of near Infra Red luciferin chemiluminescent probes. Molecular imaging of living animals is crucial to allow understanding of complex biological processes, such as ageing, diseases and studying how therapies work for lifelong health. Bioluminescence imaging (BLI) exploits the remarkable properties of a firefly enzyme (Luciferase) to emit light whilst catalysing a substrate (Luciferin) to optically image biological events in living animals. BLI would be greatly enhanced if we could increase the wavelength of light emitted to infra red light, as mammalian tissues are almost transparent at these wavelengths. We synthesised an extended luciferin and found that it gave red shifted bioluminescence of λmax 662 nm with wild type luciferase, which is competitive with the most red shifted analogues to date. In collaboration with Drs Pule and Jathoul (UCL Cancer) we have used a mutated luciferase that gives a maximum emission wavelength of 706 nm. This is the furthest red shift of any true bioluminescence system ever observed! Light emission within the nrIR range 700-850 nm can travel further in biological tissues due to the existence of a spectral window where absorption by haemoglobin, lipids and water, is low. This results in better signal fit, substantially increasing the ability to separate multiple emissions. These results illustrate the benefit of red-shifting emission for the possibility of multi-parametric BLI in animals. We are currently synthesising a derivative for X-ray studies with the enzyme and using theroretical calculations to predict what further modificiations can be made. We are actively synthesising further unusual analogues to further red shift the emitted light and improve the quantum yield. We are also synthesising nature inspired fluorescent molecules for use in imaging.

Enabling fundamental reactions of CO2. Most starting materials for the synthesis of fine chemicals are ultimately derived from petroleum. Carbon dioxide is also an important natural carbon resource and has many advantages over petroleum; it is non-toxic, nonflamable and abundant. There is also the possibility of recycling CO2 (an environmental pollutant) from industrial emissions. The possibility of using CO2 as the starting material for the synthesis of fine chemicals would be very valuable and is a chemical problem that has yet to be solved. Using our knowledge of metal oxo chemistry we have proposed a new catalytic cycle to make urethanes, which are very valuable to the chemical industry. This represents an extremely atom efficient and green synthesis of these high value compounds.

We have a number of other more speculative research projects developing new methodology for organic synthesis.

Research highlights
 

Asymmetric Intramolecular Conjugate Addition Nitro-Mannich Route to cis-2-Aryl-3-nitrotetrahydroquinolines

Anderson, J.C.; Barham, J.P.; Rundell, C.D. Org. Lett. 2015, 17, 4090-3

A Dual Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multi-Parametric Bioluminescence Imaging

Jathoul, A.P.; Grounds, H.; Anderson, J.C.; Pule, M.A. Angew. Chem. Int. Ed. 2014,53, 13059-63

An Enantioselective Tandem Reduction/Nitro-Mannich Reaction of Nitroalkenes using a Simple Thiourea Organocatalyst

Anderson, J.C.; Koovits, P.J. Chem. Sci. 2013, 4, 2897-901.                   

The Reductive nitro-Mannich Route for the Synthesis of 1,2-Diamine Containing Indolines and Tetrahydroquinolines

Anderson, J.C.; Noble, A.; Tocher, D.A. J. Org. Chem. 2012, 77, 6703-27. Feature article.

Synthesis of Ureas from Titanium Imido Complexes using CO2 as a C-1 Reagent at Ambient Temperature and Pressure

Anderson, J.C.; Bou Moreno, R. Org. Biomol. Chem. 2012, 10, 1334-8. Inside front cover.

Research Facilities
  MS, NMR
Awards
 

2006: Novartis Chemistry Lectureship

2002: Pfizer Academic Award for Chemistry

1999: SCI Young Chemist Award

1998: Zeneca Research Award in Organic Chemistry

1997: GlaxoWellcome award for Innovative Organic Chemistry

1990: Edmund White research prize for excellence in PhD research

1987: Neil Arnott prize for the top chemistry undergraduate of the University of London

1987: Governors' prize for the top chemistry undergraduate of Imperial College

Memberships
 

Fellow of the Royal Society of Chemistry

Senior Fellow of the Higher Education Academy (SFHEA)

Research interests
 
  • Asymmetric synthesis
  • Reaction methodology
  • Target synthesis
  • Nitro-Mannich reaction
  • Alpha-functionalisation of ethers
  • Synthesis of nrIR chemiluminescent and fluorescent probes
  • Developing new reactions of CO2
Teaching
 

3rd year UG core course Palladium in Organic Synthesis

4th year UG optional module Organometallics in Organic Synthesis

Laboratory demonstrating for 1st, 2nd and 3rd year lab courses

2nd year Organic tutorials

Literature and research project supervision.