Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 6, Pages 833-840Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800950
Keywords
Vitamins; Tocopherol; Biocatalysis; Enantioselectivity; Asymmetric synthesis; Enzymes; Chiral resolution
Categories
Funding
- Fundacion Ramon Areces (Madrid)
- Austrian Science Fund (FWF, Vienna, W9 DK Molecular Enzymology)
- Austrian Science Fund (FWF) [W 901] Funding Source: researchfish
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A non-lipase-based, enantiocomplementary chemoenzymatic route towards enantiopure (R)- and (S)-chromanemethanol (12), which are the key building blocks for the synthesis of stereoisomerically pure alpha-tocopherols, has been achieved by the biocatalytic resolution of a racemic 2,2-disubstituted oxirane using an epoxide hydrolase and a halohydrin dehalogenase, which exhibit opposite enantio-preferences. The introduction of chirality at an early stage of the synthesis ensured a high efficiency, leading to total overall yields of 16 and 26% for (R)- and (S)-chromanemethanol (12), respectively. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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