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Journal Article

Stereo- and regioselectivity in the P450-catalyzed oxidative tandem difunctionalization of 1-methylcyclohexene

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Roiban,  Georghe-Doru
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Agudo Torres,  Rubén
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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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

Roiban, G.-D., Agudo Torres, R., & Reetz, M. T. (2013). Stereo- and regioselectivity in the P450-catalyzed oxidative tandem difunctionalization of 1-methylcyclohexene. Tetrahedron, 69(26), 5306-5311. doi:10.1016/j.tet.2013.04.132.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0018-D5F4-8
Abstract
The selective partial oxidation of small non-functionalized molecules using biocatalysis based on P450 monooxygenases is known to be difficult due to the expected poor regio- and stereoselectivity, but in this study it was nevertheless attempted. 1-Methylcyclohexene was subjected to oxygen-mediated biocatalytic oxidation using P450-BM3 as the catalyst. Both oxidative hydroxylation and epoxidation were observed, in some cases leading to hydroxy epoxides with high diastereo- and enantioselectivity especially when employing BM3 mutants.