SYNTHESIS OF Β-METHYLPHENYLAMINES ENANTIOMERS AND THEIR HOMOLOGUES USING KINETIC ENZYMATIC SEPARATION METHOD
DOI:
https://doi.org/10.15407/dopovidi2026.02.075Keywords:
biocatalysis, arylcarboxylic acids, chiral methylphenylamines, lipase, enzymatic resolution, optical activityAbstract
The work developed a biocatalytic approach to the synthesis of enantiomerically pure β-methylphenylamines and their homologues based on the kinetic enzymatic resolution method . The key stage in the synthesis is the enzymatic resolution of racemic 3-arylbutanoic acid esters using Burkholderia cepacia lipase (Amano PS), which ensures high enantioselectivity . The obtained (R)- and (S)-arylcarboxylic acids were used as chiral precursors for the synthesis of optically pure β-methylphenylamines, as well as their homologues — (R)- and (S)-3-phenylbutan-1-amines and (R)- and (S)-4-phenylpentan-1-amines . All stages of the synthesis proceeded without racemization and with retention of the absolute configuration, as confirmed by physicochemical analytical methods . For the first time, stereoisomers of phenylpentanenitriles and 4-phenylpentan-1-amines were synthesized and characterized .
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