173065-76-4Relevant academic research and scientific papers
Chemistry of natural compounds and bioorganic chemistry: Enantioselectivity of enzymatic acylation of some structurally various racemic alcohols in anhydrous aprotic media
Gamalevich,Serebryakov
, p. 171 - 183 (1997)
Partial acylation of (R,S)-3,7-dimethyloctan-l-ol (1) and (R,S)-7-methoxy-3,7-dimethyloctan-l-ol (2) with vinyl acetate catalyzed by the lipase from Candida cylindracea affords in good yields the corresponding S-configured acetates with 92-98% enantiomeric excess (ee). Under similar conditions, racemic α-cyclogeraniol (3), drim-7-en-11-ol, methyl 4-(3-hydroxy-2-methylpropyl)benzoate, and its η6-chromium(tricarbonyl) complex (6) are acylated with rather poor (and, for the two latter, opposite) enantioselectivity, whereas (R,S)-2,4:3,5-di-O-benzylidenexylitol remains unaffected. Racemic isoborneol (8) and 2-nitro-1-phenylethanol also remain almost or completely unconverted. Attempts to perform enantioselective acylation of alcohols 3 and 8 with Ac2O in the presence of porcine pancreatic lipase (PPL) proved equally unsuccessful. By contrast, the PPL-catalyzed acylation of alcohol 6 with vinyl acetate at 17% conversion affords the levorotatory acetate (S)-6a with ca. 100% ee. PPL-Mediated partial acylation of (R,S)-pantolactone with Ac2O, followed by mild deacylation of the resulting R acetate, gives (R)-(-)-pantolactone of 97% enantiomeric purity in 60% overall yield.
A chemo-enzymatic approach to optically active 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols
Gamalevich, G. D.,Ignatenko, A. V.,Serebryakov, E. P.,Voishvillo, N. E.
, p. 743 - 748 (2007/10/02)
With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (+/-)-1, the hydrolysis of its acetate, (+/-)-2, in the presence of porcine pancreatic lipase (PPL) has been studied.Th
