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Influence of the position of the substituent on the efficiency of lipase-mediated resolutions of 3-aryl alkanoic acids
Hydrolase-catalysed kinetic resolutions to provide enantioenriched a-substituted 3-aryl alkanoic acids are described. (S)-2-Methyl-3-phenylpropanoic acid (S)-1a was prepared in 96% ee by Pseudomonas fluorescens catalysed ester hydrolysis, while, Candida antarctica lipase B (immob) resolved the a-ethyl substituted 3-arylalkanoic acid (R)-1b in 82% ee.
The influence of the position of the substituent relative to the ester site on the efficiency and enantioselectivity of the biotransformation is also explored; the same lipases were found to resolve both the a- and b-substituted alkanoic acids. Furthermore, the steric effect of substituents at the C2 stereogenic centre relative to that for their C3 substituted counterparts on the efficiency and stereoselectivity is discussed.Download Contact us