A mild chemo-enzymatic oxidation-hydrocyanation protocol

Danielle J. Vugts, Lars Veum, Kanar Al-Mafraji, Renske Lemmens, Rob F. Schmitz, Frans J.J. De Kanter, Marinus B. Groen, Ulf Hanefeld, Romano V.A. Orru

Research output: Contribution to journalArticle*Academicpeer-review

Abstract

Oxidation-hydrocyanation of γ,δ-unsaturated alcohols using (immobilised) TEMPOXPhI(OAc)2 in combination with HbHNL proceeds smoothly. After (in situ) protection, the resulting cyanohydrin derivatives were obtained in good overall yields and high ee's. A mild TEMPO-catalysed oxidation protocol is described that yields β,γ-unsaturated aldehydes without isomerisation of the double bond and that is compatible with a subsequent HbHNL-catalysed hydrocyanation performed in the same solvent system.

Original languageEnglish
Pages (from-to)1672-1677
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
Publication statusPublished - 27 Mar 2006

Keywords

  • Hydroxynitrile lyase
  • Oxidation
  • Oxynitrilase
  • TEMPO

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