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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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0001-ED27-9 Version Permalink: https://hdl.handle.net/21.11116/0000-0001-ED28-8
Genre: Journal Article

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 Creators:
Ilie, Adriana1, 2, Author           
Harms, Klaus2, Author
Reetz, Manfred T.1, 2, Author           
Affiliations:
1Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588              
2Department of Chemistry, Philipps-Universität Marburg, Hans-Meerwein Str. 4, 35032 Marburg, Germany, ou_persistent22              

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 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.

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Language(s): eng - English
 Dates: 2017-11-142018-01-092018-07-20
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.joc.7b02878
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 83 (14) Sequence Number: - Start / End Page: 7504 - 7508 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1