Journal article
Kinetic Resolution of Primary 2-methylalcohols via Pseudomonas cepacia Lipase Catalysed Enantioselective Acylation
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Författarlista: Hedenström, Erik;Högberg, Hans-Erik;Nguyen, Ba-Vu;Nordin, Ove;Vörde, Carin
Publikationsår: 2000
Startsida: 367
End page: 376
Antal sidor: 10
ISSN: 1472-7781
DOI: http://dx.doi.org/10.1039/a908023f
Visa ytterligare informaiton: View in Web of Science™
Sammanfattning
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-l-ol (E = 12), 2-methyl-5-(2-thienyl)pentan-l-ol (E=3.2) and 2-methyl-6-(2-thienyl)hexan-l-ol (E=3.8).
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