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Issue 10, 2014
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P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions

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Abstract

A variant of P450 from Bacillus megaterium five mutations away from wild type is a highly active catalyst for cyclopropanation of a variety of acrylamide and acrylate olefins with ethyl diazoacetate (EDA). The very high rate of reaction enabled by histidine ligation allowed the reaction to be conducted under aerobic conditions. The promiscuity of this catalyst for a variety of substrates containing amides has enabled synthesis of a small library of precursors to levomilnacipran derivatives.

Graphical abstract: P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions

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Publication details

The article was received on 15 May 2014, accepted on 22 Jun 2014 and first published on 10 Jul 2014


Article type: Communication
DOI: 10.1039/C4CY00633J
Author version available: Download Author version (PDF)
Citation: Catal. Sci. Technol., 2014,4, 3640-3643
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    P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions

    H. Renata, Z. J. Wang, R. Z. Kitto and F. H. Arnold, Catal. Sci. Technol., 2014, 4, 3640
    DOI: 10.1039/C4CY00633J

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