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

1Kolodiazhna, OO
Veriovka, OS
1Kolodiazhna, AO
1Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv
Dopov. Nac. akad. nauk Ukr. 2019, 7:66-74
https://doi.org/10.15407/dopovidi2019.07.066
Section: Chemistry
Language: English
Abstract: 

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.

Keywords: aminofluorocyclopentanes, biocatalysis, fluorocyclopentanols, Kazlauskas rule, lipase Burkholderia cepacia, stereochemistry
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