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A Mild Chemo‐Enzymatic Oxidation–Hydrocyanation Protocol
Author(s) -
Vugts Danielle J.,
Veum Lars,
alMafraji Kanar,
Lemmens Renske,
Schmitz Rob F.,
de Kanter Frans J. J.,
Groen Marinus B.,
Hanefeld Ulf,
Orru Romano V. A.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500905
Subject(s) - hydrocyanation , chemistry , cyanohydrin , isomerization , solvent , organic chemistry , medicinal chemistry , catalysis
Oxidation–hydrocyanation of γ,δ‐unsaturated alcohols using (immobilised) TEMPO/PhI(OAc) 2 in combination with Hb HNL 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 Hb HNL‐catalysed hydrocyanation performed in the same solvent system. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)