Kinetic Resolution of Optically Pure 3-Alkanol by Pseudomonas cepacia Lipase-Catalyzed Transesterification with Vinyl Acetate in Organic Solvent

Kinetic Resolution of Enantiomers in Racemic and Enantiomerically Enriched 2-Alkanols by <i>Pseudomonas cepacia</i> Lipase Catalyzed Transesterification with Isopropenyl Acetate in Organic Solvent

“…2) due to the reverse reaction. A similar tendency has been reported in PCL catalyzed transesterification between VA and secondary alcohol in various organic solvents (17)(18)(19).…”

“…In this paper, the bulky solvents mean those having a large cross plane perpendicular to the major axis of solvent molecule (29). In those solvents, the E values were smaller than those expected from log P. A similar tendency was observed in PCL catalyzed transesterification with TB (28,29) and also with VA (17,19).…”

“…3) because it is reported that E is independent of c (<0.5) in PCL catalyzed tranesterification between VA and racemic sulcatol in nonchlorinated solvent (toluene) (16). It was also observed that E maximized around 0. been reported for PCL catalyzed transesterfication between VA and secondary alcohol in a nonchlorinated solvent, hexane (17,19). These differences may be caused by a combination of substrate and solvent.…”

“…As shown in Figs. 2-4, the E value was eventually dependent on c. Thus, we used the previously reported equations using the optical resolution data (18,19) to resolve highly enantiomarically enriched (R)-and (S)-2-alkanols. enriched substrate (18).…”

“…In the previous papers on PCL catalyzed transesterification with secondary alcohols, we reported that E determined by Eq. (2) showed the maxima at around 0.5 of c in all systems studied (17)(18)(19) and that the reaction of enantiomerically enriched substrate was a powerful strategy for kinetic resolution of chiral compounds with high optical purity (18,19). So far, no information is available about quantitative analyses of the optical resolution data for kinetic resolution by lipase catalyzed transesterification with IPA.…”