Biocatalytic asymmetric synthesis of secondary allylic alcohols using Burkholderia cepacia lipase immobilized on multiwalled carbon nanotubes.

Abstract

The lipase from Burkholderia cepacia (BCL) was immobilized through physical adsorption on pristine and functionalized multiwalled carbon nanotubes (MWCNTs) with carboxyl or amine groups and used in the stereoselective acylation of (R,S)-1-octen-3-ol (1) and (R,S)-(E)-4-phenyl-3-buten-2-ol (4) with vinyl acetate. All immobilized preparations produced better results than free BCL. For (R,S)-4, 50% conversion and E > 200 were obtained in n-hexane or in solvent-free medium. For (R,S)-1, in solvent-free medium, the conversion was 38% with a slight increase in the E-value (E = 10).