Enzymatic resolution of norbor(NE)nylmethanols in organic media and an application to the synthesis of (+)- and (−)- endo-Norbornene lactone.

Abstract

The enzymatic resolution of some norbornene carboxylic acids, norbornenylmethanols and -methyl-amines was evaluated. The kinetic resolution of norbornyl- and norbornenylmethanols by Porcine Pancreatic Lipase (PPL)-catalyzed transesterification in methyl acetate as the solvent leads to corresponding acetates and remaining methanols both of high enantiomeric purity. A useful application is the synthesis of both enantiomers of endo-norbornene lactone 8n via transesterification of iodolactone 18 . The influence of structural variations on the efficiency of the PPL-catalyzed resolution of lactone methanols 21 , 23 , 25 and 28 , at the optimal reaction conditions established for iodolactone 18 , was investigated.