研究领域
Our research interests are broad and have in common the development and application of synthetic organic chemistry for the formation of, quite often, new and unusual chemical entities. To facilitate and enable this process we utilise state-of-the-art chemical techniques, equipment and protocols. One of our aims is to make our chemistry accessible and relatively simple to execute. Furthermore we try and exemplify our reactions using structure and function diverse substrates hopefully demonstrating as broadly as possible the scope of a particular reaction. Where possible we report substrates that have failed to react, this is often useful allowing potential users to gauge if an unknown substrate is likely to work for them.
One particular area of interest to us is the development of new synthetic methodologies that allow the efficient, atom-economic, organocatalytic formation of small strained heterocycles called aziridines. Here we have developed several routes to chiral racemic and chiral non-racemic aziridines. As well as further optimising these towards more diverse substrates our attention is also focused on utilising this methodology for the total synthesis of several natural product derived glycopeptide antibiotics for example vancomycin and analogs of vancomycin. In conjunction with these studies the chemical exploitation of our aziridine methodology for the synthesis of alternative heterocyclic motifs is currently under way as is gaining an in depth understanding of the mechanism associated with the asymmetric synthesis of the aziridines.
A second area of considerable research effort within our group is the efficient construction of calixarenes appended, principally on the upper-rim, with diverse chemical and functional groups. At the core of this is the design and synthesis of new molecular materials, which allow us to explore their properties relating these to their structure. Aspects of this work focus on using supramolecular chemistry and catalysis for the construction of man-made biomachines that mimic, for example, enzymes. Of particular interest to us is the formation of a ‘synthetic’ calixarene-derived polyketide synthase, a very large enzyme that, ordinarily, is used by Nature for secondary metabolite formation.
Our interest in calixarene chemistry has expanded into its potential use as a sensitive sensor for gold. Employing a series of specific transformations we have been able to generate a series of structure and function diverse calixarenes that demonstrate the viability of appending specific chemical handles onto the upper-rim of a calixarene allowing the new species to specifically ‘sense’ gold, even in the presence of contaminating salts from Group 1, 2 or even metals that are chemically very similar to gold, for example platinum and mercury.
Trøgers base is an interesting, readily generated bicyclic heterocycle with a well-defined V-shaped, relatively rigid 90° conformational bias. Albeit it has been known for over 125 years it has only recently been the subject of close scrutiny undergoing chemical manipulation and investigation. We are interested in further extending these studies. Thus we have initiated a research effort that aims to exploit its unusual conformational bias probing its potential in biology and medicinal chemistry, as well as investigating its utility as a conformationally bound linker within supramolecular chemistry.
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Bew, S., Hiatt-Gipson, G. D., Mills, G. P., Reeves, C.(2016)Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitratein Beilstein Journal of Organic Chemistry12.pp. 1081-1095 Full Text UEA Repository(Article)
Mills, G. P., Hiatt-Gipson, G. D., Bew, S. P., Reeves, C. E.(2016)Measurement of isoprene nitrates by GCMSin Atmospheric Measurement Techniques9.pp. 4533-4545 Full Text UEA Repository(Article)
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 conditionsin Advanced Synthesis & Catalysis357.pp. 1245-1257 Full Text UEA Repository(Article)
Anwar, A., Archibald, S., Audisio, D., Badman, G., Bergin, J., Bew, S. P., Bloom, J., Bushby, N., Busigin, A., Chan, M. Y. T., Davies, J., Dilworth, J., Dunscombe, M., Elmore, C. S., Engstrom, P., Fuchter, M. J., Geach, N. J., Georgin, D., Griffiths, A., Hansen, P., Hardcastle, G., Hiatt-Gipson, G. D., Hickey, M. J., Kitson, S. L., Lashford, A., Lenz, E., Lewinton, S., Lockley, W. J. S., Loreau, O., Maddocks, S., Marlière, P., Mcewen, A., Moody, T. S., Morgan, P., Roe, S. J., Schenk, D. J., Speed, D. J., Stockman, R. A., Sumal, K., Taran, F., Thurston, S., Waring, M., Watters., W. H.(2015)Abstracts of the 23rd International Isotope Society (UK group) Symposium: Synthesis and applications of labelled compounds 2014 Full Text()Michalska, M., Songis, O., Taillier, C., Bew, S., Dalla, V.(2014)Synergistic gold(I)/trimethylsilyl catalysis: Efficient alkynylation of N,O-acetals and related pro-electrophilesin Advanced Synthesis & Catalysis356.pp. 2040-2050 Full Text UEA Repository(Article)
Bew, S., Ashford, P., Bachera, D.(2013)Synthesis of structure and function diverse α-D-diazoacetates, α-D-diazoacetamides, α-D-diazoketones, and the antibiotic α-D-azaserinein Synthesis-Stuttgart45.pp. 903-912 Full Text UEA Repository(Article)
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 enolsin Organic Letters15.pp. 3805-3807 Full Text UEA Repository(Article)
Bew, S., Hiatt-Gipson, G., Lovell, J., Poullain, C.(2012)Mild reaction conditions for the terminal deuteration of alkynesin Organic Letters14.pp. 456-459 Full Text UEA Repository(Article)
Ashford, P., Bew, S.(2012)Recent advances in the synthesis of new glycopeptide antibioticsin Chemical Society Reviews41.pp. 957-978 Full Text UEA Repository(Article)
Savjani, N., Bew, S., Hughes, D., Lancaster, S., Bochmann, M.(2012)Reactivity of "ligand-free" Au: C-H and C-C activation versus π coordinationin Organometallics31.pp. 2534-2537 Full Text UEA Repository(Article)
Bew, S., Burrows, A., Düren, T., Mahon, M., Moghadam, P., Sebestyen, V., Thurston, S.(2012)Calix[4]arene-based metal-organic frameworks: Towards hierarchically porous materialsin Chemical communications (Cambridge, England)48.pp. 4824-4826 Full Text UEA Repository(Article)
Bew, S., Sharma, S.(2011)Do commercially available metal salts mediate calixarene formation via hydrogen-bonded dimers?in The Journal of Organic Chemistry76.pp. 7076-7083 Full Text UEA Repository(Article)
Bew, S., Sharma, S.(2011)Controlling Calixarene Size with Metal Salts: The First Brønsted-Free Synthesisin Synfacts2011.pp. 1188-1188 Full Text UEA Repository(Article)
Savjani, N., Lancaster, S., Bew, S., Hughes, D., Bochmann, M.(2011)Synthesis and structures of gold perfluorophthalimido complexesin Dalton Transactions40.pp. 1079 Full Text UEA Repository(Article)
Bew, S., Hiatt-Gipson, G.(2010)Synthesis of C -propargylic esters of N-protected amino acids and peptidesin The Journal of Organic Chemistry75.pp. 3897-3899 Full Text UEA Repository(Article)
Bew, S.(2010)Bronsted acid mediated catalytic asymmetric synthesis of aziridines UEA Repository(Paper)Bew, S.(2010)Development of a multiple asymmetric hydrogenation protocol for installing a-amino acid based structure and function complexity into calix[4]arenes UEA Repository(Paper)Bew, S.(2010)Ionic hydrogenation for the synthesis of upper-rim appended structurally diverse bis-1,3-urea calix[4]arenes and their application as an Au3+ sensor UEA Repository(Paper)Bew, S., Barter, A., Sharma, S.(2010)Mass spectroscopic investigation of bis-1,3-urea calix[4]arenes and their ability to complex N-protected α-amino acidsin Journal of Inclusion Phenomena and Macrocyclic Chemistry66.pp. 195-208 Full Text UEA Repository(Article)
Bew, S., Carrington, R., Hughes, D., Liddle, J., Pesce, P.(2009)An Organocatalytic Synthesis ofcis-N-Alkyl- andN-Arylaziridine Carboxylatesin Advanced Synthesis & Catalysis351.pp. 2579-2588 Full Text UEA Repository(Article)
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