Dr John Bower

Dr John Bower
MSc, PhD(Bristol)

Royal Society University Research Fellow

Area of research

Asymmetric catalysis, heterocyclic chemistry and total synthesis

Office N221
Cantock's Close,
Clifton, Bristol BS8 1TS
(See a map)

+44 (0) 117 928 9933
john.bower@bristol.ac.uk

Summary

Research in our group is driven by the development and discovery of new carbon-carbon and carbon-heteroatom bond forming processes. In particular, we target methods that are operationally simple, green (atom and step economy) and selective (chemo-, regio- and stereoselectivity). In this context, asymmetric transition metal-catalysed processes are of particular interest.

The discovery of fundamental reactivity naturally leads to new opportunities in synthetic methodology, total synthesis and mechanism. Current research efforts are focused upon (i) the development of new methodology for heterocyclic chemistry, (ii) the application of these processes to natural product synthesis, (iii) the evaluation of natural product analogues for medicinal purposes and (iv) understanding reaction mechanism to increase the efficiency, scope and applicability of new transformations.

Selected Publications:

1. M. H. Shaw, E. Y. Melikhova, D. P. Kloer, W. G. Whittingham and J. F. Bower*; Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium catalyzed multicomponent synthesis of N-heterobicyclic enones. J. Am. Chem. Soc. 2013, In press.

2. A. Faulkner, J. S. Scott and J. F. Bower*; Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of α,α-disubstituted dihydropyrroles and studies towards an asymmetric protocol. Chem. Commun. 2013, 49, 1521-1523.

26. T. J. Donohoe,* J. F. Bower and J. A. Basutto; Olefin cross-metathesis based approaches to furans: procedures for the preparation of di- and trisubstituted variants. Nature Protocols, 2010, 5, 2005-2010.

25. T. J. Donohoe,* N. J. Race, J. F. Bower and C. K. A. Callens; Substituted pyrroles via olefin cross-metathesis. Org. Lett. 2010, 12, 4094-4097.

24. T. J. Donohoe* and J. F. Bower; An expedient route to substituted furans via olefin cross-metathesis. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 3373-3376.

 Highlighted in Nature Chem. 2010, 2, 244.

 Commentary in Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 3279-3280.

 Highlighted as ”Editors’ Choice” in Science 2010, 327, 923.

23. J. F. Bower,* J. Rujirawanich and T. Gallagher*; N-Heterocycle construction via cyclic sulfamidates. Applications in synthesis. Org. Biomol. Chem. 2010, 8, 1505-1519.

22. T. J. Donohoe,* J. F. Bower, J. A. Basutto, L. P. Fishlock, P. A. Procopiou and C. K. A. Callens; Ring-closing metathesis for the synthesis of heteroaromatics: evaluating routes to pyridines and pyridazines. Tetrahedron. 2009, 65, Symposium-in-print, Modern applications of transition metal catalysis in heterocycle synthesis, 8969-8980.

21. T. J. Donohoe,* L. P. Fishlock, J. A. Basutto, J. F. Bower, P. A. Procopiou and A. L. Thompson; Synthesis of substituted pyridines and pyridazines via ring closing metathesis. Chem. Commun. 2009, 3008-3010.

20. J. F. Bower and M. J. Krische*; Hydrogenation for C-C bond formation. In Handbook of Green Chemistry – Green Catalysis, Volume 1: Homogeneous Catalysis. P. T. Anastas and R. H. Crabtree (Eds.), Wiley-VCH: Weinheim, 2009, 205-254.

19. J. F. Bower, I. S. Kim, R. L. Patman and M. J. Krische*; Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents. Angew. Chem. 2009, 121, 36-48; Angew. Chem. Int. Ed. 2009, 48, 34-46.

18. R. L. Patman, J. F. Bower, I. S. Kim and M. J. Krische*; Formation of C-C bonds via catalytic hydrogenation and transfer hydrogenation: vinylation, allylation and enolate addition of carbonyl compounds and imines. Aldrichimica Acta 2008, 41, 95-104.

17. J. S. Parker,* J. F. Bower, P. M. Murray, B. Patel and P. Talavera; Kepner-Tregoe decision analysis as a tool to aid route selection. Part 3. Application to a back-up series of compounds in the PDK project. Org. Process Res. Dev. 2008, 12, 1060-1077.

16. F. Shibahara, J. F. Bower and M. J. Krische*; Diene hydroacylation from the alcohol or aldehyde oxidation

level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: synthesis of ,γ-unsaturated ketones. J. Am. Chem. Soc. 2008, 130, 14120-14122.

15. R. L. Patman, V. M. Williams, J. F. Bower and M. J. Krische*; Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenyl metal reagents: a ruthenium catalyzed C-C bond forming transfer hydrogenation. Angew. Chem. 2008, 120, 5298-5301; Angew. Chem. Int. Ed. 2008, 47, 5220-5223.

 Highlighted in Org. Process Res. Dev. 2008, 12, 1021-1030.

14. F. Shibahara, J. F. Bower and M. J. Krische*; Ruthenium catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents. J. Am. Chem. Soc. 2008, 130, 6338-6339.

Publications Dr John F. Bower

 Highlighted as “News of the Week“ in Chem. Eng. News 2008, 86, 10.

 Highlighted in SYNFACTS 2008, 831.

13. J. F. Bower, R. L. Patman and M. J. Krische*; Iridium catalyzed C-C coupling via transfer hydrogenation: carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene. Org. Lett. 2008, 10, 1033-1035.

 Highlighted in SYNFACTS 2008, 505.

12. J. F. Bower, E. Skucas, R. L. Patman and M. J. Krische*; Catalytic C-C coupling via transfer hydrogenation: reverse prenylation, crotylation and allylation from the alcohol or aldehyde oxidation level. J. Am. Chem. Soc. 2007, 129, 15134-15135.

 Highlighted in SYNFACTS 2008, 293.

11. E. Skucas, J. F. Bower and M. J. Krische*; Carbonyl allylation in the absence of preformed allyl metal reagents: reverse prenylation via iridium catalysed hydrogenative coupling of dimethylallene. J. Am. Chem. Soc. 2007, 129, 12678-12679.

10. J. F. Bower, P. Szeto and T. Gallagher*; Cyclic sulfamidates as precursors to alkylidene pyrrolidines and piperidines. Org. Lett. 2007, 9, 4909-4912.

9. J. F. Bower, P. Szeto and T. Gallagher*; Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin. Org. Lett. 2007, 9, 3283-3286.

8. J. F. Bower, A. J. Williams, H. Woodward, P. Szeto, R. M. Lawrence and T. Gallagher*; Reactivity of cyclic sulfamidates towards phosphonate-stabilised enolates: synthesis and applications of -phosphono lactams. Org. Biomol. Chem. 2007, 5, 2636-2644.

7. J. F. Bower, T. Riis-Johannessen, P. Szeto, A. J. Whitehead and T. Gallagher*; Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin. Chem. Commun. 2007, 728-730.

 Highlighted in SYNFACTS 2007, 574.

6. J. F. Bower, P. Szeto and T. Gallagher*; Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine. Org. Biomol. Chem. 2007, 5, 143-150.

5. J. F. Bower, S. Chakthong, J. Švenda, A. J. Williams, R. M. Lawrence, P. Szeto and T. Gallagher*; Reactivity of cyclic sulfamidates towards sulfur-stabilised enolates. Stereocontrolled synthesis of functionalised lactams. Org. Biomol. Chem. 2006, 4, 1868-1877.

4. J. F. Bower, P. Szeto and T. Gallagher*; Cyclic sulfamidates as lactam precursors. An efficient asymmetric synthesis of (-)-aphanorphine. Chem. Commun. 2005, 5793-5795.

3. J. F. Bower, J. Švenda, A. J. Williams, J. P. H. Charmant, R. M. Lawrence, P. Szeto and T. Gallagher*; Cyclic sulfamidates as vehicles for the synthesis of substituted lactams. Org. Lett. 2004, 6, 4727-4730.

3. A. Faulkner and J. F. Bower*; Highly efficient Narasaka-Heck cyclizations mediated by P(3,5-(CF₃)₂C₆H₃)₃: facile access to N-heterobicyclic scaffolds. Angew. Chem. Int. Ed. 2012, 51, 1675-1679.

Biography

John Bower obtained his M.Sci. degree in Chemistry in 2003 from the University of Bristol. He then remained at Bristol to study for his Ph.D. degree (2007) under the guidance of Professor Timothy Gallagher. During this time his research focused on the development of cyclic sulfamidate based N-heterocyclic methodologies and their application to natural product synthesis. His first postdoctoral appointment (2007-2008) was with Professor Michael Krische at the University of Texas at Austin where he investigated transfer hydrogenative strategies for carbonyl addition. He then undertook a second postdoctoral appointment with Professor Timothy Donohoe at the University of Oxford where he focussed on the use of olefin cross metathesis for heteroaryl synthesis. In 2010, he was awarded a Royal Society University Research Fellowship and commenced his independent career at the University of Bristol. The group’s research interests lie broadly within the area of asymmetric catalysis with a particular focus on metal-catalysed processes and their application to heterocyclic chemistry. A special emphasis is placed on the development of green processes (i.e. atom economy, step economy and selectivity).

Curriculum vitae