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Biocatalytic Route to Chiral Acyloins: P450-Catalyzed Regio- and Enantioselective α-Hydroxylation of Ketones

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Agudo Torres,  Rubén
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Roiban,  Georghe-Doru
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Lonsdale,  Richard
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Ilie,  Adriana
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Reetz,  Manfred T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Citation

Agudo Torres, R., Roiban, G.-D., Lonsdale, R., Ilie, A., & Reetz, M. T. (2015). Biocatalytic Route to Chiral Acyloins: P450-Catalyzed Regio- and Enantioselective α-Hydroxylation of Ketones. The Journal of Organic Chemistry, 80(2), 950-956. doi:10.1021/jo502397s.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0027-B62E-D
Abstract
P450-BM3 and mutants of this monooxygenase generated by directed evolution are excellent catalysts for the oxidative α-hydroxylation of ketones with formation of chiral acyloins with high regioselectivity (up to 99%) and enantioselectivity (up to 99% ee). This constitutes a new route to a class of chiral compounds that are useful intermediates in the synthesis of many kinds of biologically active compounds.