Philip Bulman Page

Philip Bulman Page

Professor Emeritus, Professor

  • 3.01 Chemistry

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Personal profile

Biography

Professor Philip Page is a graduate of the Imperial College, University of London (1978), from where he also obtained his PhD in 1981 in the area of organic synthesis, working with Prof Steve Ley FRS. He then spent two years working for Professor Leo Paquette at Ohio State University as an SERC/NATO Research Fellow before moving to the University of Liverpool as a lecturer in 1983, and subsequently to Loughborough University as Professor of Organic Chemistry in 1996. He has published over 240 articles, and has won a Nuffield Foundation Science Research Fellowship, the Royal Society of Chemistry Hickinbottom Fellowship, the Glaxo Wellcome Award for Innovative Chemistry, the Royal Society of Chemistry Tilden Medal & Lectureship, and a Royal Society Industry Fellowship. In 2007, he moved to the Chair of Organic Chemistry at UEA. His research interests lie principally in the areas of asymmetric synthesis/catalysis, synthetic methodology and natural product synthesis. Professor Page, a Kentish Man, is married and currently lives in Norfolk with one wife and two cats. His hobbies include chemistry, reading, hifi and music, not necessarily all at once, and food and drink.

 

Selected Publications:

‘Asymmetric Oxidation of Enol Derivatives to α-Alkoxy Carbonyls Using Iminium Salt Catalysts: A Synthetic and Computational Study,’ P C B Page, S. Almutairi, Y Chan, G R Stephenson, Y Gama, R L Goodyear, A Douteau, S M Allin, G A Jones, J. Org. Chem.201984, 554-669. DOI: 10.1021/acs.joc.8b02354 

‘Novel Binaphthyl and Biphenyl α- and β-Amino Acids and Esters: Organocatalysis of Asymmetric Diels-Alder Reactions. A Combined Synthetic and Computational Study,’ P C B Page, F Kinsey, Y Chan, I Strutt, A. M. Z. Slawin, G A Jones, Org. Biomol. Chem.201816, 7400-7416. DOI: 10.1039/c8ob01795f 

‘Formal Total Synthesis of (+)-C9-Deoxyomuralide from L-leucine Using a Double Sacrificial Chirality Transfer Approach,’ P C B Page, R L Goodyear, A E Horton, Y Chan, R Karim, M O’Connell, C J Hamilton, A M Z Slawin, B R Buckley, S M Allin, J. Org. Chem.201782, 12209-12223. DOI: 10.1021/acs.joc.7b02078 

‘Asymmetric Epoxidation of Chromenes Mediated by Iminium Salts: Synthesis of Mollugin and (3S,4R)-trans-3,4-Dihydroxy-3,4-Dihydromollugin,’P C B Page, Y Chan, Abu Hassan Noor Armylisas, M Alahmdi, Tetrahedron201672, 8406-8416. DOI: 10.1016/j.tet.2016.10.070  

‘Ruthenium-Free Preparation of 1,5-Disubstituted Triazoles by Alkylative Debenzylation of 1,4-Disubstituted Triazoles,’ P C B Page, G R Stephenson, J M Harvey, A M Z Slawin, Synlett2016, 2500-2504. DOI: 10.1055/s-0035-1562603 

‘“Janus” calixarenes: double–sided molecular linkers for facile, multi-anchor point, multi-functional, surface modification,’ J P Buttress, D P Day, J Courtney, E J Lawrence, D L Hughes, A Crossley, S E Matthews, P C B Page, C Redshaw, G G Wildgoose, Langmuir201632, 7806-7813. DOI: 10.1021/acs.langmuir.6b02222 

‘Convenient access to mesobenzylic bis-alkynes,’ P C B Page, G R Stephenson, J M Harvey, A-C Gaumont, C Alayrac, A M Z Slawin, Synlett201627, 961-964. DOI: 10.1055/s-0035-1561318. 

‘New Biphenyl Iminium Salt Catalysts for Highly Enantioselective Asymmetric Epoxidation: Role of Additional Substitution and Dihedral Angle,’ P C B Page, C J Bartlett, Y Chan, S M Allin, M J McKenzie, J Lacour, G A Jones, Org. Biomol. Chem.,201614, 4220-4232. DOI: 10.1039/c6ob00542j 

 

 

External Activities

 

  • 1998- current Editor-in-Chief, ‘Synthetic Communications’
  • 2001- 2011 Scientific Editor, Annual Reports, Section B, Royal Society of Chemistry
  • 1999- 2002 Secretary, Royal Society of Chemistry Heterocyclic Group
  • 1999- 2002 Member, Scientific Advisory Board, Synetix
  • 1999- current Co-Founder & Scientific Director, Charnwood Molecular Ltd
  • 2005- 2007 International Academic Advisor to the Institute of Science, UiTM, Malaysia
  • 2004- 2008 Royal Society Industry Fellow 

 

Key Research Interests and Expertise

  • Research in this group has concentrated in the 'core science' area of organic synthesis, primarily in three interrelated themes: the discovery of new reactions, the invention of new stereocontrolled processes, especially for asymmetric synthesis, and the application of new chemical ideas to natural product synthesis. We have been, in general, interested in discovering new reactions and reagents, and in applying our chemistry to problems in synthesis. The major areas are outlined below. 

 

Natural Product Synthesis

The design of efficient and elegant pathways for the synthesis of complex natural products remains a fascinating and testing area for research in organic chemistry. 

Asymmetric Synthesis

The search for new and ever more selective reactions, especially for asymmetric synthesis, is one of the most important and challenging topics for research today. We have been interested in developing new methods for the enantioselective control of organic reactions. This research falls into three main areas:

  • Atom-transfer catalysts and reagents for oxidation, epoxidation and aziridination
  • The development of novel ligand systems for metal-mediated transformations
  • New asymmetric systems for chiral recognition


Atom-Transfer Catalysts and Reagents:  Sulfoxidation

We have developed new methods for the enantioselective control of organic reactions, and a particularly important development was the discovery of a new and highly enantioselective catalytic system for asymmetric oxidation, for example of sulfides (illustrated left) and alkenes. This system, which uses hydrogen peroxide as the oxidant and an optically pure sulfonylimine as chiral mediator, is remarkably simple to carry out, requires no preparation and isolation of sensitive reagent, no close monitoring, and provides remarkably clean reactions in an inexpensive and environmentally friendly process.

Atom-Transfer Catalysts and Reagents: Epoxidation

We have applied some of the key ideas of this process to the challenging area of catalytic asymmetric epoxidation of alkenes. Our approach employs imminium ion salts as catalysts in the presence of either OxoneTM or tetraphenylphosphonium mono-peroxysulfate (TPPP) as the stoichiometric oxidant. Investigations using asymmetric tetrahydroisoquinolinium salts have provided promise the simple and mild procedure described with unprecidented ees of up to 97%. This has resulted in the highly enantioselective syntheses of a number of natural products.

Atom-Transfer Catalysts and Reagents:  Nitrogen-Transfer

Also with potential application in the area of atom-transfer processes, we have reported the first stable enantiomerically pure N-H oxiziridines. We are actively investigating their application as chiral electrophilic nitrogen-transfer agents. This approach offers an interesting alternative to the traditional chiral auxiliary chemistry.

Chiral Recognition Agents: Calix[4]resorcinarene Derivatives

We have described the first enantioselective syntheses of a number of enantiomerically pure calix[4]resoricinarene derivatives. Our route enables ready access to multigram quantities of the diastereoisomerically pure tetrakis(benzoxazines) (below) in a short route starting from resorcinol and dodecanal. Subsequent transformation provides C4n symmetric calix[4]resorcinarene derivatives as single enantiomers. The residual phenol and secondary amine groups allow for further functionalistaion and the possibility of accessing a wide range of axially chiral calix[4]resorcinarene derivatives. We are actively preparing materials of this type and investigating their application in the areas of chiral recognition and asymmetric catalysis. 

Research Group Membership

 

Recent Past Group Members: 

 Y Chan                                   2002-16

L Appleby                                2005-08                                    

C-E Roy                                   2005-08                                    

C A C Bordogna                       2005-08                                    

A Mace                                    2006-09                                    

C Gillings                                 2006-09                                    

C Elliott                                   2006-09                                    

F Frimpong                               2007-11                                    

C Bartlett                                  2008-11                                    

C Pearce                                   2008-11                                    

M de Kiss                                 2008-11                                    

W-W Wang                              2008-11                                    

D Day                                      2009-12                                    

A Sheldon                                2009-12                                    

I Strutt                                      2009-13                                    

M Alahmdi                               2009-13                                    

T Dixon                                    2010-13                                    

A Abu Hassan                           2010-13                                    

B Mahoney                               2010-13                                    

L Ardemani                              2010-11                                    

A Horton                                  2011-15                                    

A Nabi                                     2011-12                                    

S Almutairi                               2011-15                                    

J Harvey                                   2011-15                                    

C Macarov                                2011-15                                    

N Alsenani                               2012-17                                    

F Kinsey                                   2012-15                                    

J Martin                                    2012-16                                    

S Packman                                2012-13                                    

J Buttress                                  2012-15                                    

L Tull                                       2013-14                                    

Y Gama                                    2014-17                                    

R Goodyear                              2015-18                                    

G Hughes                                 2015-19                                    

B Alfulaiti                                2015-16                                    

A Wright                                  2016-19                                    

 

Specialisms

Organic chemistry; asymmetric synthesis; asymmetric catalysis; organic synthesis.

Network

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