Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 23, Pages 3031-3035Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800569
Keywords
Alcohols; Organocatalysis; Oxidation; Oxidoreductases
Categories
Funding
- European Union's Horizon 2020 MSCA ITN-EID program [634200]
- Ministerio de Ciencia e Innovacion of Spain [CTQ 2014-55015]
- Principado de Asturias [FC-15-GRUPIN-14-002]
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An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98%). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95% yield, >99% ee, >99: < 1 dr).
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