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

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.

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 Creators:
Roiban, Georghe-Doru1, Author           
Agudo Torres, Rubén1, Author           
Reetz, Manfred T.1, 2, Author           
Affiliations:
1Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588              
2Philipps-Universität Marburg, Fachbereich Chemie, ou_persistent22              

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Free keywords: Enantioselectivity; CH-activation; P450; Monooxygenase; Diastereoselectivity
 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.

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 Dates: 2013-07-01
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/j.tet.2013.04.132
ISSN: 0040-4020
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
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Publ. Info: -
Pages: - Volume / Issue: 69 (26) Sequence Number: - Start / End Page: 5306 - 5311 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773