P450-catalyzed regio- and stereoselective oxidative hydroxylation of 
disubstituted cyclohexanes: creation of three centers of chirality in a single 
CH-activation event

Ilie, Adriana; Agudo Torres, Rubén; Roiban, Georghe-Doru; Reetz, Manfred T.

doi:10.1016/j.tet.2014.11.067

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P450-catalyzed regio- and stereoselective oxidative hydroxylation of disubstituted cyclohexanes: creation of three centers of chirality in a single CH-activation event

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

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Citation

Ilie, A., Agudo Torres, R., Roiban, G.-D., & Reetz, M. T. (2015). P450-catalyzed regio- and stereoselective oxidative hydroxylation of disubstituted cyclohexanes: creation of three centers of chirality in a single CH-activation event. Tetrahedron, 71(3), 470-475. doi:10.1016/j.tet.2014.11.067.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-B958-4

Abstract

Wild-type P450-BM3 is able to catalyze in a highly regio- and diastereoselective manner the oxidative hydroxylation of non-activated disubstituted cyclohexane derivatives lacking any functional groups, including cis- and trans-1,2-dimethylcyclohexane, cis- and trans-1,4-dimethylcyclohexane, and trans-1,4-methylisopropylcyclohexane. In all cases except chiral trans-1,2-dimethylcyclohexane as substrate, the single hydroxylation event at a methylene group induces desymmetrization with simultaneous creation of three centers of chirality. Certain mutants increase selectivity, setting the stage for future directed evolution work.