Kinetic resolution of primary 2-methyl-substituted alcohols via Pseudomonas cepacia lipase-catalysed enantioselective acylation

The enantioselectivities of lipases from Pseudomonas cepacia (PFL, Amano PS , etc.) towards a series of primary 2-methyl-substituted alcohols using vin yl acetate as the acyl donor in transesterifications in organic solvents we re studied. In terms of enantioselectivity, the best results were found for 3-aryl-2-methylpropan-1-ols with enantiomeric ratios (E-values) over 100 i n most cases, whereas other 3-substituted primary 2-methylpropan-1-ols gene rally displayed lower enantioselectivities: 3-cycloalkyl-2-methylpropan-1-o ls (E approximate to 20) and 2-methylalkan-1-ols (E approximate to 10). Mov ing the aryl group closer or further away from the chiral centre resulted i n low enantioselectivities: 2-arylpropan-1-ols (E < 10), 2-methyl-4-(2-thie nyl)butan-1-ol (E = 12), 2-methyl-5-(2-thienyl)pentan-1-ol (E = 3.2) and 2- methyl-6-(2-thienyl)hexan-1-ol (E = 3.8).