title: Preparative-scale Enzyme-catalyzed Synthesis of (R)-α-Fluorophenylacetic Acid.
abstract: A preparative-scale asymmetric synthesis of (R)-α-fluorophenylacetic acid, a useful chiral derivatizing reagent, is described. Starting from ethyl α-bromophenylacetate, α-fluorophenylmalonic acid dipotassium salt was prepared in three steps (54% yield), including nucleophilic substitution by the fluoride ion as the keystep. Both the purified form and crude preparation of arylmalonate decarboxylase in E. coli worked well on this substrate, and (R)-α-flurophenylacetic acid (>99% e.e.) was prepared in a quantitative yield.
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: Y
authors.initials: Y
authors.lastname: Fukuyama
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: K
authors.initials: K
authors.lastname: Matoishi
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: M
authors.initials: M
authors.lastname: Iwasaki
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: E
authors.initials: E
authors.lastname: Takizawa
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: M
authors.initials: M
authors.lastname: Miyazaki
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: H
authors.initials: H
authors.lastname: Ohta
authors.affiliation: b Tokyo Research Center, Tosoh Corp.
authors.forename: S
authors.initials: S
authors.lastname: Hanzawa
authors.affiliation: b Tokyo Research Center, Tosoh Corp.
authors.forename: H
authors.initials: H
authors.lastname: Kakidani
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: T
authors.initials: T
authors.lastname: Sugai
keywords: (R)-α-fluorophenylacetic acid; arylmalonate decarboxylase; asymmetric decarboxylation; α-fluorophenylmalonic acid