ChemInform Abstract: Enzymatic Resolution of Norbor(ne)nylmethanols in Organic Media and an Application to the Synthesis of (+)- and (-)-endo-Norbornene Lactone.

Abstract

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.