LIPASE-CATALYZED ENANTIOSELECTIVE SYNTHESIS OF NAPHTHYL TRIFLUOROMETHYL CARBINOLS AND THEIR CORRESPONDING NON-FLUORINATED COUNTERPARTS

Enantioselective synthesis of both enantiomers of beta- and alpha-naphthyl trifluoromethyl carbinols (R)1a, (s)-1a, (R)-2a, (S)-2a has been achieved through acylation of the corresponding racemic alcohols (RS)-1a and (RS)-2a with vinyl acetate in the presence-of lipase PS. The effect of fluorine atoms on the extent and enantioselectivity of the process has been tested by carrying out the same biocatalytic transformation on their non-fluorinated counterparts (RS)-1b and (RS)-2b. The order of reactivity follows the trend (RS)-1b > (RS)2b approximate to (RS)-1a > (RS)-2a. Effect of the hydrophobicity of the solvent in the resolution of (RS)-1a is also presented.