4.8 Article

Laccase/TEMPO-mediated system for the thermodynamically disfavored oxidation of 2,2-dihalo-1-phenylethanol derivatives

Journal

GREEN CHEMISTRY
Volume 16, Issue 5, Pages 2448-2453

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4gc00066h

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Funding

  1. Spanish Ministerio de Ciencia e Innovacion [MICINN-12-CTQ2011-24237]
  2. Principado de Asturias [SV-PA-13-ECOEMP-42, SV-PA-13-ECOEMP-43]
  3. Universidad de Oviedo [UNOV-13-EMERG-01, UNOV-13-EMERG-07]
  4. MICINN

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An efficient methodology to oxidize beta,beta-dihalogenated secondary alcohols employing oxygen was achieved in a biphasic medium using the laccase from Trametes versicolor/TEMPO pair, providing the corresponding ketones in a clean fashion under very mild conditions. Moreover, a chemoenzymatic protocol has been applied successfully to deracemize 2,2-dichloro-1-phenylethanol combining this oxidation with an alcohol dehydrogenase-catalyzed bioreduction.

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