Authors: Hedin-Dahlström J
, Shoravi S
, Wikman S
, Nicholls IA
Stereoselective reduction of menthone by molecularly imprinted polymers.
Publication date: 2004
Journal: Tetrahedron: Asymmetry
Alternative URL: http://www.sciencedirect.com/science/article/B6THT-4D2G5N5-5/2/97d9027fe9c8a9a371e11f578ea8adc1
Abstract: Polymeric chiral reductants selective for the reduction of (-)-menthone 1 to the diastereomeric products (-)-menthol 2 and (+)-neomenthol 3 were prepared by a covalent molecular imprinting using 2 as the template. The LiAlH4 derivatized imprinted polymers altered the natural outcome of the reduction reaction (LiAlH4) from 2:1 [(-)-menthol:(+)-neomenthol] to 1:1. The reaction mechanism is discussed in terms of reaction site structure. The molecularly imprinted polymers demonstrated enantioselective recognition for 2 (0.15 μmol enantioselective sites/g polymer) in batch binding experiments
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