Tetrahedron p. 4231 - 4240 (1990)
Update date:2022-08-05
Topics:
Rabiller, C. G.
Koenigsberger, .
Faber, K.
Griengl, H.
Aiming to improve the enantioselectivity of enzymatic resolution of esters, lipase catalyzed hydrolysis of (D)- and (L)-2-chloropropanoates of four racemic alcohols and transesterification of ethyl (DL)-2-chloropropanoate with optically pure alcohols was investigated.Thus, (rac)-endo-2-norbornyl (L)-2-chloropropanoate was hydrolized by lipase P about 5 times more selectively than its corresponding (D)-counterpart and optically pure (1R,2S,5R)-menthol was obtained by transesterification of its racemate with ethyl (D)-2-chloropropanoate using Candida cylindracea (CC)lipase.From the results obtained it seems obvious that lipases CC and P mainly can recognize the chirality of an alcohol moiety rather than that of an acid
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