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

Renata, Hans and Wang, Z. Jane and Kitto, Rebekah Z. and Arnold, Frances H. (2014) P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions. Catalysis Science and Technology, 4 (10). pp. 3640-3643. ISSN 2044-4753. PMCID PMC4159215. doi:10.1039/c4cy00633j. https://resolver.caltech.edu/CaltechAUTHORS:20140714-152320951

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/c4cy00633jDOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4159215PubMed CentralArticle
ORCID:
AuthorORCID
Renata, Hans0000-0003-2468-2328
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2014 The Royal Society of Chemistry. Received 15 May 2014, Accepted 22 Jun 2014; First published online 10 Jul 2014. We thank Dr. S. Virgil and the Center for Catalysis and Chemical Synthesis (3CS) at Caltech for assistance with chiral SFC. This research was supported by the Gordon and Betty Moore Foundation through grant GBMF2809 to the Caltech Programmable Molecular Technology Initiative. Z. J. Wang was supported by a Ruth L. Kirschtein NRSA postdoctoral fellowship from the National Institutes of Health (5F32EB015846). We thank Mr. C. C. Farwell and Dr. J. A. McIntosh for helpful discussions. We thank Dr. K. M. Engle for assistance with variable temperature NMR. The content of this paper is solely the responsibility of the authors and does not represent the official views of any of the funding agencies.
Funders:
Funding AgencyGrant Number
Gordon and Betty Moore FoundationGBMF2809
NIH Postdoctoral Fellowship5F32EB015846
Issue or Number:10
PubMed Central ID:PMC4159215
DOI:10.1039/c4cy00633j
Record Number:CaltechAUTHORS:20140714-152320951
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20140714-152320951
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:47189
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:14 Jul 2014 22:56
Last Modified:10 Nov 2021 17:36

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