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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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Article information


Submitted
15 May 2014
Accepted
22 Jun 2014
First published
10 Jul 2014

Catal. Sci. Technol., 2014,4, 3640-3643
Article type
Communication
Author version available

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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