Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 48, Pages 15852-15856Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201810059
Keywords
carbene transfer; cyclopropanation; myoglobin; nitrile-substituted cyclopropanes; protein engineering
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Funding
- U.S. National Institute of Health [GM098628]
- U.S. National Science Foundation [CHE-0946653, CHE-1725028]
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A chemobiocatalytic strategy for the highly stereo-selective synthesis of nitrile-substituted cyclopropanes is reported. The present approach relies on an asymmetric olefin cyclopropanation reaction catalyzed by an engineered myoglobin in the presence of ex situ generated diazoacetonitrile within a compartmentalized reaction system. This method enabled the efficient transformation of a broad range of olefin substrates at a preparative scale with up to 99.9% de and ee and up to 5600 turnovers. The enzymatic product could be further elaborated to afford a variety of functionalized chiral cyclopropanes. This work expands the range of synthetically valuable, abiotic transformations accessible through biocatalysis and paves the way to the practical and safe exploitation of diazoacetonitrile in biocaialytic carbene transfer reactions.
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