Bull Group Publications

15.

Synthesis of cis-C-Iodo-N-Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography

Boultwood, T.; Affron, D. P.; Trowbridge, A. D.; Bull, J. A. J. Org. Chem. 2013, 78, 6632–6647.

Open access (ACS Author Choice)

 

12. 

Highly cis-selective synthesis of iodo-aziridines using diiodomethyllithium and in situ generated N-Boc-imines

Bull, J. A.; Boultwood, T.; Taylor, T. A. Chem. Commun. 2012, 48, 12246-12248.

pdf open access

11.

Catalytic Enantioselective Synthesis of Secondary Alkylboronate Building Blocks With and Without Metals

Bull, J. A. Angew. Chem., Int. Ed. 2012, 51, 8930-8932.


Highlight Review

Abstract With or without you: Chiral secondary alkylboronates can now be accessed by highly enantioselective catalytic methods including conjugate addition under metal-free conditions with an NHC catalyst, and also iridium-catalyzed hydrogenation. These methods reinforce the potential of secondary alkylboronates as ideal and universal chiral building blocks for bond formation to sp3 carbon atoms.



10. Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines

Charette, A. B.; Bull, J. A.; Mousseau, J. J.; Pelletier, G. Chem. Rev. 2012, 112, 2642-2713.

Review Article


9. Synthesis of 2- and 2,3-substituted pyrazolo[1,5-a]pyridines: scope and mechanistic considerations of a domino direct alkynylation and cyclization of N-iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes

Mousseau, J. J.; Bull, J. A.; Ladd, C. L.; Fortier, A.; Sustac Roman, D.; Charette, A. B. J. Org. Chem. 2011, 76, 8243-8261.


8. Preparation of (E)-(2-Iodovinyl)benzene from Benzyl Bromide and Diiodomethane

Bull, J. A.; Mousseau, J. J.; Charette, A. B. Org. Synth. 2010, 87, 170-177.


7. Intramolecular Simmons-Smith Cyclopropanation. A Study into Alkyl-Substituted Zinc Carbenoids, Directing Group Effects and the Synthesis of Bicyclo[n.1.0]alkanes

Bull, J. A.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 1895-1902.


6. Copper-Catalyzed Direct Alkenylation of N-Iminopyridinium Ylides

Mousseau, J. J.; Bull, J. A.; Charette A. B. Angew. Chem. Int. Ed. 2010, 49, 1115-1118.

Highlighted in: Methods of Organic Synthesis #68931.


5. Convenient One-Pot Synthesis of (E)-β-Aryl Vinyl Halides from Benzyl Bromides and Dihalomethanes

Bull, J. A.; Mousseau, J. J.; Charette, A. B. Org. Lett. 2008, 10, 5485-5488.

Highlighted in: www.ACS.org Noteworthy Chemistry 12 Jan 2009.

Highlighted in: Organic Chemistry Portal (www.organic-chemistry.org/abstracts/lit2/379.shtm)


4. Improved Procedure for the Synthesis of gem-Diiodoalkanes by the Alkylation of Diiodomethane. Scope and Limitations

Bull, J. A.; Charette, A. B. J. Org. Chem. 2008, 73, 8097-8100.


3. N-4-Pyrimidinyl-1H-indazol-4-amine Inhibitors of Lck: Indazoles as Phenol Isosteres with Improved Pharmacokinetics

Bamborough, P.; Angell, R. M.; Bhamra, I.; Brown, D.; Bull, J.; Christopher, J. A.; Cooper, A. W. J.; Fazal, L. H.; Giordano, I.; Hind, L.; Patel, V. K.; Ranshaw, L. E.; Sims, M. J.; Skone, P. A.; Smith, K. J.; Vickerstaff, E.; Washington, M. Bioorg. Med. Chem. Lett. 2007, 17, 4363–4368.


2. Total Synthesis of Potent Antifungal Marine Bisoxazole Natural Products Bengazoles A
and B

Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Chem. Eur. J. 2007, 13, 5515-5538.


1. Stereocontrolled Total Synthesis of Bengazole A: A Marine Bisoxazole Natural Product Displaying Potent Antifungal Properties

Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Angew. Chem. Int. Ed. 2006, 45, 6714-6718; Angew. Chem. 2006, 118, 6866.

14.

Copper-Catalyzed N-Arylation of 2-Imidazolines with Aryl Iodides

Davis, O. A.; Hughes, M.; Bull, J. A. J. Org. Chem. 2013, 78, 3470-3475.

16.

2-(Aryl-Sulfonyl)Oxetanes as Designer 3-Dimensional Fragments for Fragment Screening: Synthesis and Strategies for Functionalisation

Morgan, K. F.; Hollingsworth, I. A.; Bull, J. A. Chem. Commun. 2014, 50, 5203–5205.

Featured as part of the 2014 ChemComm Emerging Investigators Issue

James featured: Chem. Commun. 2014, 50, 5100-5114

pdf open access

18.

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Boultwood, T.; Affron, D. P.; Bull, J. A. J. Vis. Exp. 2014, 87, e51633.


JoVE is a video methods journal. 

Abstract: Our protocol for the diastereoselective one-pot preparation of cis-N-Ts-iodoaziridines is described. The generation of diiodomethyllithium, addition to N-Ts aldimines and cyclization of the amino gem-diiodide intermediate to iodoaziridines is demonstrated. Also included is our protocol to rapidly and quantitatively assess the most appropriate stationary phase for purification by flash chromatography.

17.

A Molecular Rotor for Measuring Viscosity in Plasma Membranes of Live Cells

López-Duarte, I.; Vu, T. T.; Izquierdo Arcusa, M.; Bull, J. A.;  Kuimova, M. K. Chem. Commun. 2014, 50, 5282–5284.


Molecular rotors have emerged as versatile probes for microscopic viscosity in live cells, however, the exclusive localisation of rotors in the plasma membrane has remained elusive. We report the synthesis, spectroscopic characterisation and live cell imaging of a new BODIPY-based molecular rotor suitable for mapping viscosity in the cell plasma membrane.

20.

Regio and Stereospecific Synthesis of C-3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp3)-H Arylation

Affron, D. P.; Davis, O. A.; Bull, J. A. Org. Lett. 2014, 16, 4956-4959.

Open access (ACS Author Choice)

Highlighted in ACS Select Virtual Issue on Recent Advances in C–H Functionalization

James' Publications: PhD & Postdoc

Davis, O. A.; Bull, J. A. Angew. Chem. Int. Ed. 2014, 53, 14230-14234.

pdf open access

Davis, O. A.; Bull, J. A. Synlett 2015, 26, 1283-1288.

Invited submission as Synpacts highlight

pdf

Morgan, K. F.; Hollingsworth, I. A.; Bull, J. A. Org. Biomol. Chem. 2015, 13, 5265-5272.

Zenzola, M.; Doran, R.; Luisi, R; Bull, J. A. J. Org. Chem. 2015, 80, 6391-6399.

Open access (ACS Author Choice)

Boultwood, T.; Affron, D. P.; Bull, J. A. Tetrahedron 2015, 71, 4949-4957.

26.

Imaging Phase Separation in Model Lipid Membranes Through the use of BODIPY Based Molecular Rotors

Dent, M. R; López-Duarte, I.; Dickson, C. J.; Geoghegan, N. D.; Cooper, J. M.; Gould, I. R.; Krams, R.; Bull, J. A.; Brooks, N. J.; Kuimova, M. K. Phys. Chem. Chem. Phys. 2015, 17, 18393-18402.


In order to fully understand the dynamics of processes within biological lipid membranes, it is necessary to possess an intimate knowledge of the physical state and ordering of lipids within the membrane. Here we report the use of three molecular rotors based on meso-substituted boron-dipyrrin (BODIPY) in combination with fluorescence lifetime spectroscopy to investigate the viscosity and phase behaviour of model lipid bilayers. .... [more]

Davis, O. A.; Croft, R. A.; Bull, J. A. Chem. Commun. 2015, 51, 15446-15449.

pdf open access

Highlighted as Synfact of the month

Morgan, K. F.; Doran, R.; Croft, R. A.; Hollingsworth, I. A.; Bull, J. A. Synlett 2016, 27, 106-110.

Special issue celebrating the 70th birthday of Prof Steven V. Ley.

pdf

30.

Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

Zenzola, M.; Doran, R.; Degennaro, L.; Luisi, R; Bull, J. A. Angew. Chem. Int. Ed. 2016, 55, 7203-7207.

open access pdf

For a video demonstrating the protocol see: https://youtu.be/4KpDQnGHi28

For SI, including details of robustness screen of conditions see: supinfo

31.

Oxetanes: Recent Advances in Synthesis, Reactivity and Medicinal Chemistry

Bull, J. A.; Croft, R. A.; Davis, O. A.; Doran, R.; Morgan K. F. Chem. Rev. 2016, 116, 12150-12233.

open access

Croft, R. A.; Mousseau, J. J.; Choi, C.; Bull, J. A. Chem. Eur. J. 2016, 22, 16271-16276.

open access

Highlighted as a “Hot Paper”

Highlighted in ChemViews Editors' Choice: Spotlights section

Davis, O. A.; Croft, R. A.; Bull, J. A. J. Org. Chem. 2016, 81, 11477–11488.

34.

Synthesis of NH-Sulfoximines from Sulfides by Chemoselective One-Pot N- and O-Transfers

Tota, A.; Zenzola, M.; Chawner, S. J.; St John-Campbell, S.; Carlucci, C.; Romanazzi, G.; Degennaro, L.;

Bull, J. A.; Luisi, R. Chem. Commun. 2017, 53, 348-351.

35.

Imaging tumor microscopic viscosity in vivo using molecular rotors

Shimolina, L.E.; Angeles Izquierdo, M.; López-Duarte, I.; Bull, J. A.; Shirmanova, M. V.; Klapshina, L. G.; Zagaynova, E. V.; Kuimova, M. K. Sci. Rep. 2017, 7, 4197.


The microscopic viscosity plays an essential role in cellular biophysics by controlling the rates of diffusion and bimolecular reactions within the cell interior. While several approaches have emerged that have allowed the measurement of viscosity and diffusion on a single cell level in vitro, the in vivo viscosity monitoring has not yet been realized. Here we report the use of fluorescent molecular rotors in combination with Fluorescence Lifetime Imaging Microscopy (FLIM) to image microscopic viscosity in vivo, both on a single cell level and

... [more]

36.

Visualising membrane viscosity of porcine eye lens cells using molecular rotors

Sherin, P.S.; López-Duarte, I.; Dent, M. R.; Kubánková, M.; Vyšniauskas, A.; Bull, J. A.; Reshetnikova, E. S.; Klymchenko, A. S.; Tsentalovicha, Y. P.; Kuimova, M. K. Chem. Sci. 2017, 8, 3523-3528.


The plasma membranes of cells within the eye lens play an important role in metabolite transport within the avascular tissue of the lens, maintaining its transparency over the entire lifespan of an individual. Here we use viscosity-sensitive ‘molecular rotors’ to map the microscopic viscosity within these unusual cell membranes, establishing that they are characterised by an unprecedentedly high degree of lipid organisation.

37.

Probing supramolecular protein assembly using covalently attached fluorescent molecular rotors

Kubánkováa, M.; López-Duarte, I.; Bull, J. A.; Vadukul, D.; Serpell, L.; de Saint Victor, M.; Stride, E.; Kuimova, M. K. Biomaterials 2017, 139, 195-201.


Changes in microscopic viscosity and macromolecular crowding accompany the transition of proteins from their monomeric forms into highly organised fibrillar states. Previously, we have demonstrated that viscosity sensitive fluorophores termed ‘molecular rotors’, when freely mixed with monomers of interest, are able to report on changes in microrheology accompanying amyloid formation, and measured an increase in rigidity of approximately three orders of magnitude during aggregation of lysozyme and insulin. Here we extend this strategy by covalently attaching molecular rotors to several proteins capable of assembly into fibrils, namely lysozyme, fibrinogen and beta-amyloid peptide. ...[more]

39.

Straightforward Strategies for the Preparation of NH-Sulfoximines: A Serendipitous Story

Bull, J. A.; Degennaro, L.; Luisi, R. Synlett 2017, in press,.