Portal de Periódicos da CAPES

Preparative-scale Enzyme-catalyzed Synthesis of ( R )-α-Fluorophenylacetic Acid

1999; Oxford University Press; Volume: 63; Issue: 9 Linguagem: Inglês

10.1271/bbb.63.1664

1347-6947

Yasuaki Fukuyama, Kaori Matoishi, Masakazu Iwasaki, Eiji Takizawa, Mamoru Miyazaki, Hiromichi Ohta, Satoshi Hanzawa, Hitoshi Kakidani, Takeshi Sugai,

Chemical Synthesis and Analysis

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.