Biography

Click here for current PhD opportunities in CHE. But feel free to email me to discuss projects outside these areas and alternative sources of funding.

School Positions:

Reader in Chemistry; Chair, Chemistry Organic MSc Examination Board; Staff co-chair, CHE Staff-Student Liaison Committee and CHE Partnership Officer; CHE NSS Champion; and a member of the CHE Special Circumstances Panel.
 
Download Richard's CV here (PDF format)

The Stephenson group works in the field of synthetic organic chemistry and methodologies for enantioselective synthesis. Our targets are functional molecules with a variety of applications including functionalised calix[n]arenes and multi-cavitands as novel receptors and switchable NLOphores, helicenes for use in Two Photon Circular Dichroism (TPCD), bioactive compounds targeting neglected tropical diseases (NTDs) and as potential anti-cancer leads by the inhibition of ubiquitin ligase, and novel reagents for cellulose derivatisation for biocomposite applications. Current projects in the group also focus on the concept of double/multi-kinetic resolution (multi-KR), and asymmetric ‘click’ chemistry, and the applications of these new concepts in the synthesis of tetrathia[7]helicenes (multi-KR) and hexaazahelicenes (our ‘click’ helicenes). International collaborations play a significant part in our work; with photophysics experts at the University of Leuven for nonlinear optics (NLO) and TPCD, with laboratories in subSaharan Africa in the ‘Open Lab Africa’ project, and with three research groups at the South University of Science and Technology of China (SUSTech)  as part of the UEA-SUSTech Split-Site PhD Programme.

Dr G. Richard Stephenson, FRSC, CChem, started his career as a Research Fellow at the Australian National University (Canberra) and a Senior Research Fellow at Girton College, Cambridge, before moving to UEA, first as a Royal Society University Research Fellow, and then as Lecturer, Senior Lecturer and Reader. In 2000, Stephenson was Visiting Professor at the Université de Caen; in 2001, Invited Professor at Université Paris VI; and in 2003, he was Invited Professor at the Université Catholique de Louvain. Stephenson held a Visiting Fellowship at the Australian National University in 2006, and was UEA’s lead investigator in the ‘Innovative Synthesis: Chemistry and Entrepreneurship’ (IS:CE-chem) and ‘Academy-Industry Chemistry-Channel’ (AIcc) EU Interreg IVA projects (2009-2015), which together have contributed 2.5 million euros of ERDF funding to the Organic Sector in the School of Chemistry and supported 15 PhD students in the Science Faculty at UEA. Stephenson is a Fellow of the Royal Society of Chemistry (RSC) and a member of the American Chemical Society (ACS).

Selected Publications

Stephenson, G. Richard; Doulcet, Julien.
Kinetic resolutions of tetrathia[7]helicene derivatives by (–)-sparteine mediated enantioselective lithiation.
Chem. Eur. J. 2015. 21, 18677-18689
DOI: 10.1002/chem.201502958

Stephenson, G. Richard; Doulcet, Julien.
Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes.
Chem. Eur. J. 2015, 21, 13431-13436)
DOI: 10.1002/chem.201501627

Bew, Sean P.; Stephenson, G. Richard; Rouden, Jacques; Ashford, Polly-Anna; Hiatt-Gipson, Glyn D.: Bourane, Manuel; Charvet, Agathe; Dalstein, Virginie M. D.; Jauseau, Raphael; Hiatt-Gipson, Glyn D.; Martinez-Lozano, Luis A
Bioinspired, Base- & Metal-free, Mild, Decarboxylative Aldol Activation of Malonic Acid Half Thioesters Under Phase-Transfer Reaction Conditions.
Adv. Synth. Catal. 2015, 357, 1245-1257
DOI: 10.1002/adsc.201400915

Bew, Sean P.; Stephenson, G. Richard, Rouden, Jacques; Godemert, I.; Seylani Haseena Martinez-Lozano, Luis A.
Gaining an insight into reactivity differences between malonic acid half thioester (MATH) and malonic acid half oxyesters (MAHO).
Chem. Eur. J. 2017 published on line
DOI: 10.1002/chem.201605148

All Publications

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Bew, S. P., Stephenson, G. R., Rouden, J., Godemert, J., Seylani, H., Martinez-Lozano, L. A.

(2017)

Gaining insight into reactivity differences between malonic acid half thioester (MAHT) and malonic acid half oxyesters (MAHO),

in Chemistry - A European Journal

23

(19)

pp. 4557–4569

Full Text UEA Repository

(Article)

(Published)


Bulman Page, P., Stephenson, R., Harvey, J., Gaumont, A., Alayrac, C., Slawin, A.

(2016)

Convenient access to meso benzylic bis-alkynes,

in Synlett

27

(06)

pp. 961-964

Full Text UEA Repository

(Article)

(Published)


Glowacka, P., Stephenson, G.

(2016)

One-pot synthesis of 9-aminomethylanthracene,

in Synlett

27

(11)

pp. 1733-1737

Full Text UEA Repository

(Article)

(Published)


Bulman Page, P. C., Stephenson, G. R., Harvey, J., Slawin, A. M. Z.

(2016)

Ruthenium-Free Preparation of 1,5-Disubstituted Triazoles by Alkylative Debenzylation of 1,4-Disubstituted Triazoles,

in Synlett

27

(17)

pp. 2500-2504

Full Text UEA Repository

(Article)

(Published)


Glowacka, P. C., Maindron, N., Richard Stephenson, G., Romieu, A., Renard, P., Emery, F. D. S.

(2016)

Synthesis and photophysical properties of iron-carbonyl complex-coumarin conjugates as potential bimodal IR-fluorescent probes,

in Tetrahedron Letters

57

(45)

pp. 4991–4996

Full Text UEA Repository

(Article)

(Published)


Bew, S. P., Stephenson, G. R., Rouden, J., Ashford, P. A., Bourane, M., Charvet, A., Dalstein, V. M. D., Jauseau, R., Hiatt-Gipson, G. D., Martinez-Lozano, L. A.

(2015)

Bioinspired, base- and metal-free, mild decarboxylative aldol activation of malonic acid half thioesters under phase-transfer reaction conditions,

in Advanced Synthesis & Catalysis

357

(6)

pp. 1245-1257

Full Text UEA Repository

(Article)

(Published)


Doulcet, J., Stephenson, G. R.

(2015)

Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes,

in Chemistry - A European Journal

21

(38)

pp. 13431–13436

Full Text UEA Repository

(Article)

(Published)


Doulcet, J., Stephenson, G. R.

(2015)

The use of (–)-sparteine/organolithium reagents for the enantioselective lithiation of 7,8-dipropyltetrathia[7]helicene: single and double kinetic resolution procedures,

in Chemistry - A European Journal

21

(51)

pp. 18677-18689

Full Text UEA Repository

(Article)

(Published)


Stephenson, G., Cauteruccio, S., Doulcet, J.

(2014)

Comparison of Ullmann/RCM and Ullmann/Bis-hydrazone Coupling Reactions; New Access to Benzodithiophenes for Dye-Sensitized Solar Cell and Thiahelicene Applications,

in Synlett

25

(05)

pp. 701-707

Full Text UEA Repository

(Article)

(Published)


Cauteruccio, S., Dova, D., Graiff, C., Carrara, C., Doulcet, J., Stephenson, G. R., Licandro, E.

(2014)

A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes,

in New Journal of Chemistry

38

(6)

pp. 2241-2244

Full Text UEA Repository

(Article)

(Published)


Stephenson, G., Palotai, I.

(2013)

Regiodirecting effects in difunctionalised tricarbonyl[(1,2,3,4,5-η)-cyclohexadienyl]iron(1+) salts: building blocks for alkaloids,

in Tetrahedron Letters

54

(2)

pp. 123-127

Full Text UEA Repository

(Article)

(Published)


Stephenson, G. R., Buttress, J., Deschamps, D., Lancelot, M., Martin, J., Sheldon, A., Alayrac, C., Gaumont, A., Bulman Page, P.

(2013)

An Investigation of the Asymmetric Huisgen 'Click' Reaction,

in Synlett

24

(20)

pp. 2723-2729

Full Text UEA Repository

(Article)

(Published)


Bew, S., Stephenson, G., Rouden, J., Martinez-Lozano, L., Seylani, H.

(2013)

Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols,

in Organic Letters

15

(15)

pp. 3805-3807

Full Text UEA Repository

(Article)

(Published)


Stephenson, G., Palotai, I. M., Thomas, S., Tinkl, M.

(2013)

Synthetic studies for the 1,3-iterative organoiron approach to the synthesis of siculinine: efficient arylation using a diarylcuprate reagent,

in European Journal of Organic Chemistry

2013

(10)

pp. 1895–1901

Full Text UEA Repository

(Article)

(Published)


Stephenson, G., Anson, C., Malkov, A., Roe, C.

(2012)

Influencing the Balance between ipso and ω Nucleophile Addition to (1-Arylcyclohexadienyl)iron Intermediates in Alkaloid Synthesis,

in European Journal of Organic Chemistry

2012

(25)

pp. 4716-4732

Full Text UEA Repository

(Article)

(Published)


Monteforte, M., Cauteruccio, S., Maiorana, S., Benincori, T., Forni, A., Raimondi, L., Graiff, C., Tiripicchio, A., Stephenson, G., Licandro, E.

(2011)

Tetrathiaheterohelicene Phosphanes as Helical-Shaped Chiral Ligands for Catalysis,

in European Journal of Organic Chemistry

2011

(28)

pp. 5649-5658

Full Text UEA Repository

(Article)

(Published)


Stephenson, G. R., Anson, C. E., Creaser, C. S., Daul, C. A.

(2011)

Spectroscopic, Structural and DFT Study of the Responses of Carbonylmetal Crown Ether Complexes to Alkali Metal Cations,

in European Journal of Inorganic Chemistry

(13)

pp. 2086-2097

Full Text UEA Repository

(Article)

(Published)


Stephenson, G. R., Roe, C., Sandoe, E. J.

(2011)

Electrophilic C-12 Building Blocks for Alkaloids: 1,1 Iterative Organoiron-Mediated Routes to (+/-)-Lycoramine and (+/-)-Maritidine,

in European Journal of Organic Chemistry

(9)

pp. 1664-1681

Full Text UEA Repository

(Article)

(Published)


Stephenson, G., Anson, C., Swinson, G.

(2011)

Biphenyl-cis-diol chemistry to access enantiopure aryl-substituted organoiron complexes,

in Tetrahedron Letters

52

(28)

pp. 3547-3550

Full Text UEA Repository

(Article)

(Published)


Roe, C., Sandoe, E. J., Stephenson, G. R.

(2010)

Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes,

in Tetrahedron Letters

51

(4)

pp. 591-595

Full Text UEA Repository

(Article)

(Published)


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Key Research Interests

Double and Multi-Kinetic Resolution
Enantioselective synthesis is an important goal and conventional methods rely on asymmetric induction or classical/kinetic resolution, in which a chiral auxiliary is used at a specific step to gain access to non-racemic samples. In our multi-KR approach, the all the steps of a retrosynthetic analysis are assessed for the possibility of chiral intervention and prioritised. As the synthesis proceeds, a series of kinetic resolutions progressively improves the enantiomeric excess (e.e.) until the level is high enough to allow the product crystallise as a single enantiomer. Whereas the conventional approach can sometime require extensive and time-consuming optimisation at a specific step (a potential ‘bottle-neck’), the multi-KR approach allows additional KR steps to be introduced into the synthetic plan to further improve e.e. if the original selection for KRs lack the required levels of stereorecognition. There are two important advantages to multi-KR: no individual step needs full optimisation, and once enantiopurity has been achieved, further work to optimise stereoselectivity improves the chemical yield of the synthesis (e.g. for scale-up), not the enantioselectivity. The double-KR approach has been exemplified in our work on tetrathiahelicines (see selected publications), and research in this area now moves to apply the concept in general to the synthesis of natural products and bioactives.

Asymmetric ‘click’ chemistry
Because the 1,2,3-triazoles lack chirality, until our work in this area, the famous Sharpless/Mendal CuAAC ‘click’ reaction had been performed only once with chiral auxiliaries on the copper. Our aim is to generalise the asymmetric variant of ‘click’ chemistry by studying the desymetrisation of diynes, including, for the first time, conceptually important meso diynes. Compared with the many thousands of papers on ‘click’ chemistry, there are still only a handful on asymmetric ‘click’ chemistry, but this total grows more rapidly as other research groups pick up this topic which is set to become a major and highly competitive research area. Our aim is to develop the method as a general strategy in asymmetric synthesis to take prochiral diyne starting materials on to enantiopure final products which exploit the properties of 1,2,3-triazoles as ligating (including bioligating) sites in novel series of chiral ligands and bioactives, and as part of the fused aromatic ring systems of helicenes (see below).

Enantioselective Synthesis of Helicenes
The twisted pi systems of helicenes provide a unique class of organic structures in which the two ends of a series of ortho-fused aromatic rings can no longer lie in the same plane because they overlap. Such structures are chiral and when there is sufficient overlap, the barrier to epimerisation is high. Our interest in helicenes springs from their potential in nonlinear optics (NLO), and particularly their predicted but as yet unrealised special suitability for use in Two Photon Circular Dichroism (TPCD), a goal which will lead ultimately to a new method of bioimaging which combines the confocality of two-photon absorption with the sensitivity to the stereochemical environment demonstrated in circular dichroism spectroscopy. Current target molecules in the group include tetrathia[7]helicenes addressed by a one-pot double-KR approach, and a new class of hexaazahelicenes than can be accessed by a double asymmetric ‘click’ strategy. Both conventional ‘single-dipole full-turn’ and our novel ‘double-dipole half turn’ designs are targets for the group.

Ubiquitin Ligase Inhibitors
Ubiquitin ligases are enzymes which are implicated in tumour outgrowth and spread and so are attractive targets for new approaches to develop anticancer bioactives (PI: Chantry). As a synthetic chemistry component of a larger collaborative project with Chantry, Hemmings, Page (Schools of Biological Sciences and Chemistry) we are working on the design and synthesis of new and more potent inhibitors for E3 ubiquitin ligases employing a fragment-based strategy which involves the synthesis of small binding motifs and linkers, assisted by modelling studies to aid the molecular design process.

‘Open Lab Africa’
The neglected tropical diseases (NTDs) still cause great human suffering in some of the poorest countries on the planet. The UEA ‘Open Lab Africa’ project is adopting a fresh and novel approach to this global challenge in a collaborative effort with Duvendack, Gallash, Hamilton, McDermott, (Schools of Development Studies, Law, and Pharmacy) at UEA and Frey (University of Southampton) together with institutes in Cameroon, Democratic Republic of the Congo, Ghana, Kenya, Tanzania, and Uganda. The synthetic chemistry part of the project involves the identification and synthesis of new lead structures and their analogues in a fragment-based approach towards new capabilities to address particular NTDs which are of most serious or growing concern in the subSaharan region of Africa. The project combines an Open Lab-Book and Open Med-Chem approach which invites institutes and specialists around the world to follow, advise, and even join in the project.

UEA-SUSTech Split-Site PhD Projects
Three research topics are being performed in collaboration with the South University of Science and Technology of China (SUSTech) as part of the UEA-SUSTech Split-Site PhD Programme: synthesis of bioactive meroterpenoids as leads to target new treatments for neglected tropical diseases (with Dr Jing Xu; xuj@sustc.edu.cn), desymmetrisation by application of chiral organocatalysts in the type II intramolecular [5+2] cycloaddition reaction (with Dr Chuangchuang Li; ccli@sustc.edu.cn) and extended associative polymerization exploiting molecular recognition in orthogonal difunctional (with Prof. Zhong-Ren: chenzr@sustc.edu.cn). Enquiries concerning PhD studentship opportunities in these topics, which will involve research work in both Norwich (UK) and Shenzhen (China), should be addressed initially to the Chinese co-supervisors because pre-selection for the award of UEA-SUSTech Split-Site studentships is being performed at SUSTech.

Research Funding


Leverhulme Trust
Asymmetric 'click'-synthesis of helicenes
Stephenson, GR
27-Mar-17 – 26-Mar-19
£ 166,029

InnovateUK
Towards fully sustainable high-performance biocomposites for lightweight vehicles
Stephenson, GR
01-Apr-16 – 31-Mar-18
£ 285,179

EU Interreg IVA
Academie-Industrie Chemistry Channel (A-I chem channel)
Stephenson, GR
02-Nov-11 – 30-June-2015
€ 988,444

EPSRC
Highly anisotopic helicene-based NLOphores for two photon circular dichroism
Stephenson, GR
01-Oct-09 – 30-Sept-13
£ 270,570

EU Interreg IVA
Innovative Synthesis: Chemistry and Entrepreneurship (IS:CE chem)
Stephenson, GR
01-June-08 – 30-Sept-13
€ 1,597,285

Daphne Jackson Trust
Introducing a new twist to photonics
Fellowship for K. Hamilton
01-July-08 – 30-June-10
£ 38,817
 
EPSRC
Nanoscale and molecular photonics
Meech, SR, Cammidge, AN, Andrews, DL, Reading, M, Stephenson, GR, Mayes, AG and Barker, S
01-Sep-05 - 31-Aug-07
£255,840

EPSRC
EU COST Chemistry D26: European collaboration for calculation inspired synthesis of NLO responsive aryl and helicenyl organometallics Stephenson, GR
01-Jul-06 - 31-Jul-07
£20,414

EPSRC
Enantioselective organoiron / heterocycloaddition approach to hippeastrine
Stephenson, GR
01-Mar-03 - 31-Mar-06
£82,497

EPSRC
European collaboration to synthesise and evaluate NLO compounds with novel photorefractive properties
Stephenson, GR
30-Jul-02 –
29-Jan-06
£21,041

SmithKline Beecham
CASE Award: Custom synthesis and automated evaluation to optimise the asymmetric Heck reaction
Stephenson, GR
01-Oct-01 - 30-Sep-04
£20,550

CEC
Organometallic dipoles with NLO properties
Stephenson, G R
01-Mar-98 – 28-Feb-02
£114,400

CSL
Studentship: Synthesis of stable-isotope-labelled lipids for nutritional studies
Stephenson, G R and Shepherd, MJ (CSL)
01-Oct-98 - 30-Sep-01
£42,747

GlaxoWellcome
CASE Award: Develop catalytic versions of stoichiometric organometallic reactions
Stephenson, G R
01-Oct-98 - 30-Sep-01
£18,000

 

Research Group Membership

PhD students

  • James Tonkin
  • Greg Hughes*
  • Adam Wright*

* indicates collaborative project

Postdoctoral Visiting Fellows

  • Ken Hamilton
  • Lloyd Sayer

Senior Technical Officer

MSc students

External Activities and Indicators of Esteem

EU activites:

  • Member COST D2 Working Group
  • Coordinator COST D4 Working Group
  • Coordinator EU TMR RTN
  • Coordinator COST D14 Working Group
  • Member COST COST D26 Working Group
  • Interreg Trans-Manche projects IS:CE chem and AI chem Chennel

International invitations (professional):

  • March-April 2006: Visiting Fellow: Australian National University
  • October 2003: Invited Professor: Université Catholique de Louvain (CHIM 3430)
  • October 2002: Colloque 3e Cycle Universitaire de Suisse Occidental, (Commission Scientifique pour L'Enseignment du 3e Cycle en Chimie)
  • April 2001: Invited Professor: Université PARIS VI

Book Chapters:

  • 2004-5 - "Handbook of Functionalised Organometallics"[Wiley-VCH, Weinheim, (ISBN 3-527-31131-9)]"
  • 2004 - "Bioorganometallic Chemistry" [Wiley-VCH, Weinheim, (ISBN 3-527-30990-X)]
  • 2001 - "Science of Synthesis; Houben-Weyl Methods of Molecular Transformations" [Georg Theime Verlag, Stuttgart (ISBN 3-13-112131-9)]

Reviews:

  • Highlights: Organic Chemistry’ in Chemistry and Industry, published by the Society of Chemical Industry

Professional:

  • Fellow of the Royal Society of Chemistry, Chartered Chemist,
  • Member of the American Chemical Society