P450-Catalyzed Regio- and Stereoselective Oxidative Hydroxylation of 
6-Iodotetralone: Preparative-Scale Synthesis of a Key Intermediate for 
Pd-Catalyzed Transformations

Ilie, Adriana; Harms, Klaus; Reetz, Manfred T.

doi:10.1021/acs.joc.7b02878

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P450-Catalyzed Regio- and Stereoselective Oxidative Hydroxylation of 6-Iodotetralone: Preparative-Scale Synthesis of a Key Intermediate for Pd-Catalyzed Transformations

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

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

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Citation

Ilie, A., Harms, K., & Reetz, M. T. (2018). P450-Catalyzed Regio- and Stereoselective Oxidative Hydroxylation of 6-Iodotetralone: Preparative-Scale Synthesis of a Key Intermediate for Pd-Catalyzed Transformations. The Journal of Organic Chemistry, 83(14), 7504-7508. doi:10.1021/acs.joc.7b02878.

Cite as: https://hdl.handle.net/21.11116/0000-0001-ED27-9

Abstract

Chiral alcohols are important building blocks for the production of pharmaceuticals, catalytic access being possible by the use of enzymes, transition metal catalysts, or organocatalysts. Herein we report the use of cytochrome P450-BM3 mutants for the oxidative hydroxylation of 6-iodotetralone regio- and enantioselectively at C4 with formation of the (R)-alcohol. This CH activation is not possible using modern synthetic catalysts. The synthetic utility of this valuable synthon was explored in palladium-catalyzed coupling reactions that occur in the absence of undesired racemization.