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Updated: Apr 23, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions
Hans Renata1, Z Jane Wang1, Rebekah Z Kitto1
1Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC-210-41, Pasadena, CA.
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.
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