Stereoselective bioreduction for the resolution of racemic mixtures of bicyclo[3.3.1]nonane-2,6-dione using vegetables

Abstract

► For the enantioseparation of racemic bicyclo[3.3.1]nonane-2,6-dione, vegetables of the family Apiaceae were found to be suitable. ► Reaction conditions were optimized using celery roots. ► (+)-Enantiomer of bicyclo[3.3.1]nonane-2,6-dione was obtained with the optical purity of 90–98% and the yield of more than 90%. Screening of various vegetables as biocatalysts for the stereoselective bioreduction and resolution of racemic bicyclo[3.3.1]nonane-2,6-dione was performed. Vegetables of the family Apiaceae , i.e. the roots of parsnip ( Pastinaca sativa ), celery ( Apium graveolens ), parsley ( Petroselinum crispum ) and carrot ( Daucus carota ) were found to be the best. The methodology described here allows the efficient enantioseparation of (+)-enantiomer of bicyclo[3.3.1]nonane-2,6-dione. The reaction time, temperature and the amount of celery roots were optimized and (+)-enantiomer was obtained with the optical purity of 90–98% and the yield of more than 90%.