A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Protocol

Oxidation–hydrocyanation of γ,δ‐unsaturated alcohols using (immobilised) TEMPO/PhI(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 des...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2006-04, Vol.2006 (7), p.1672-1677
Main Authors: Vugts, Danielle J., Veum, Lars, al-Mafraji, Kanar, Lemmens, Renske, Schmitz, Rob F., de Kanter, Frans J. J., Groen, Marinus B., Hanefeld, Ulf, Orru, Romano V. A.
Format: Article
Language:English
Subjects:
Hydroxynitrile lyase
Oxidation
Oxynitrilase
TEMPO
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Summary:Oxidation–hydrocyanation of γ,δ‐unsaturated alcohols using (immobilised) TEMPO/PhI(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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500905