Kinetic resolution of primary 2-methyl-substituted alcohols via Pseudomonas cepacia lipase-catalysed enantioselective acylation
- 1 January 2000
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 367-376
- https://doi.org/10.1039/a908023f
Abstract
The enantioselectivities of lipases from Pseudomonas cepacia (PFL, Amano PS, etc.) towards a series of primary 2-methyl-substituted alcohols using vinyl acetate as the acyl donor in transesterifications in organic solvents were studied. In terms of enantioselectivity, the best results were found for 3-aryl-2-methylpropan-1-ols with enantiomeric ratios (E-values) over 100 in most cases, whereas other 3-substituted primary 2-methylpropan-1-ols generally displayed lower enantioselectivities: 3-cycloalkyl-2-methylpropan-1-ols (E ≈ 20) and 2-methylalkan-1-ols (E ≈ 10). Moving the aryl group closer or further away from the chiral centre resulted in low enantioselectivities: 2-arylpropan-1-ols (E < 10), 2-methyl-4-(2-thienyl)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).Keywords
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