title: P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions.
abstract: A variant of P450 fromBacillus megateriumfive 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.
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC-210-41, Pasadena, CA.
authors.forename: Hans
authors.initials: H
authors.lastname: Renata
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC-210-41, Pasadena, CA.
authors.forename: Z Jane
authors.initials: ZJ
authors.lastname: Wang
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC-210-41, Pasadena, CA.
authors.forename: Rebekah Z
authors.initials: RZ
authors.lastname: Kitto
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC-210-41, Pasadena, CA.
authors.forename: Frances H
authors.initials: FH
authors.lastname: Arnold