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stereospecific rearrangements of cyclic N-aryl benzyllithiums. Key
aspects include the application of four novel imine reductases, and
the stereospecific functionalisation of configurationally stable
benzylic organolithium derivatives of nitrogen heterocycles. The
products constitute a new class of functionalized azepanes and
benzazepines of potential utility as drug molecules.
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Experimental desriptions for chemistry and biocatalysis;
spectroscopic data for all new compounds.
AUTHOR INFORMATION
Corresponding Authors
nicholas.turner@manchester.ac.uk; j.clayden@bristol.ac.uk
Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENTS
(8) Brown, D. G.; Bernstein, P. R.; Wu, Y.; Urbanek, R. A.; Becker, C. W.;
Throner, S. R.; Dembofsky, B. T.; Steelman, G. B.; Lazor, L. A.; Scott, C.
W.; Wood, M. W.; Wesolowski, S. S.; Nugiel, D. A.; Koch, S.; Yu, J.;
Pivonka, D. E.; Li, S.; Thompson, C.; Zacco, A.; Elmore, C. S.; Schroeder,
P.; Liu, JW.; Hurley, C. A.; Ward, S.; Hunt, H. J., Williams, K.;
McLaughlin, J.; Hoesch, V.; Sydserff, S.; Maier, D.; Aharony, D. Azepines
and Piperidines with Dual Norepinephrine Dopamine Uptake Inhibition and
Antidepressant Activity. ACS Med. Chem. Lett. 2013, 4, 46–51.
This work was support by the BBSRC (studentship to W.Z.),
EPSRC, ERC, and Johnson Matthey (CASE studentship to
S.L.M.). We thank Prozomix Ltd. for their financial support to
J.R.M. and assistance in the cloning and production of enzymes.
N.J.T. thanks the American Chemical Society for the ACS
Catalysis lectureship.
(9) Ahmad, S.; Sutherland, A. Stereoselective Synthesis of Hydroxylated
3-Aminoazepanes Using a Multi-Bond Forming, Three-Step Tandem
Process. Org. Biomol. Chem. 2012, 10, 8251–8259.
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