Enzymatic synthesis of enantiomerically pure 1,2-fluorocyclopentanols and 1,2-aminofluorocyclopentanes

• Main Authors: O.O. Kolodiazhna, O.S. Veriovka, A.O. Kolodiazhna
• Format: Article
• Language: English
• Published: Publishing House "Akademperiodyka" 2019-07-01
• Series: Доповiдi Нацiональної академiї наук України
• Subjects: aminofluorocyclopentanes; biocatalysis; fluorocyclopentanols; Kazlauskas rule; lipase Burkholderia cepacia
• Online Access: http://dopovidi-nanu.org.ua/en/archive/2019/7/9

Vicinal fluorocyclopentanol are valuable chiral synthetic blocks for the preparation of a number of natural and synthetic biologically active substances Racemic cis-2-fluorocyclopentanols were separated into enantiomers by the kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media, High enantioselectivity (ee > 98 %) and good yields of compounds were obtained for all substrates using Burkholderia cepacia lipase, The fluorocyclopentanols were converted into enantiomerically pure 1,2-aminofluorocyclopentanes using the Mitsunobu reaction, The enantiomeric purity of the compounds was determined by Mosher's acid derivatization method, and the absolute configurations were determined using the Kazlauskas rule.