Recognition of the remote chiral center in lipase-catalyzed kinetic resolution of [2-methyl-2-(2′-naphthyl)-1,3-benzodioxol-4-yl]methyl acetate, the precursor of 2-methyl-2-(2′-naphthyl)-1,3-benzodioxole-4-carboxylic acid (MNB carboxylic acid)

- Burkholderia cepacia lipase (Amano PS-IM) recognized a remote chiral center of [2-methyl-2-(2′-naphthyl)-1,3-benzodioxol-4-yl]methyl acetate.
- B. cepacia lipase (Amano PS-IM)-catalyzed kinetic resolution of racemic acetate proceeded highly enantioselectively (E = 72) to give (R)-alcohol.
- The results of molecular dynamics simulations suggest that the tetrahedral intermediate complex of lipase with (R)-acetate, the fast isomer, was more stable than that with (S)-acetate, the slow isomer.
- Repetitive use of B. cepacia lipase and direct oxidation of alcohol provided both enantiomers [(R)-: 99.4% ee and (S)-: 99.4% ee] of MNB carboxylic acid as methyl esters.