Published October 2, 2014
| Supplemental Material + Accepted Version + Published
Journal Article
Open
P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions
Chicago
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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.
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.Attached Files
Published - c4cy00633j.pdf
Accepted Version - nihms612519.pdf
Supplemental Material - c4cy00633j1_si.pdf
Files
nihms612519.pdf
Additional details
- PMCID
- PMC4159215
- Eprint ID
- 47189
- Resolver ID
- CaltechAUTHORS:20140714-152320951
- Gordon and Betty Moore Foundation
- GBMF2809
- NIH Postdoctoral Fellowship
- 5F32EB015846
- Created
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2014-07-14Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field