A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade

D.J. Vugts, L. Veum, K. Al-Mafraji, R.H. Lemmens, R.F. Schmitz, F.J.J. de Kanter, M.B. Groen, U. Hanefeld, Orru R.V.A.

Research output: Contribution to JournalArticleAcademicpeer-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. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Original languageEnglish
Pages (from-to)1672
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusPublished - 2006

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cascades
Oxidation
oxidation
Isomerization
aldehydes
Aldehydes
isomerization
alcohols
Alcohols
Derivatives
TEMPO
cyanohydrin

Cite this

Vugts, D. J., Veum, L., Al-Mafraji, K., Lemmens, R. H., Schmitz, R. F., de Kanter, F. J. J., ... R.V.A., O. (2006). A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade. European Journal of Organic Chemistry, 1672. https://doi.org/10.1002/ejoc.200500905
Vugts, D.J. ; Veum, L. ; Al-Mafraji, K. ; Lemmens, R.H. ; Schmitz, R.F. ; de Kanter, F.J.J. ; Groen, M.B. ; Hanefeld, U. ; R.V.A., Orru. / A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade. In: European Journal of Organic Chemistry. 2006 ; pp. 1672.
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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. {\circledC} Wiley-VCH Verlag GmbH & Co. KGaA, 2006.",
author = "D.J. Vugts and L. Veum and K. Al-Mafraji and R.H. Lemmens and R.F. Schmitz and {de Kanter}, F.J.J. and M.B. Groen and U. Hanefeld and Orru R.V.A.",
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Vugts, DJ, Veum, L, Al-Mafraji, K, Lemmens, RH, Schmitz, RF, de Kanter, FJJ, Groen, MB, Hanefeld, U & R.V.A., O 2006, 'A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade' European Journal of Organic Chemistry, pp. 1672. https://doi.org/10.1002/ejoc.200500905

A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade. / Vugts, D.J.; Veum, L.; Al-Mafraji, K.; Lemmens, R.H.; Schmitz, R.F.; de Kanter, F.J.J.; Groen, M.B.; Hanefeld, U.; R.V.A., Orru.

In: European Journal of Organic Chemistry, 2006, p. 1672.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade

AU - Vugts, D.J.

AU - Veum, L.

AU - Al-Mafraji, K.

AU - Lemmens, R.H.

AU - Schmitz, R.F.

AU - de Kanter, F.J.J.

AU - Groen, M.B.

AU - Hanefeld, U.

AU - R.V.A., Orru

PY - 2006

Y1 - 2006

N2 - 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. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

AB - 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. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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DO - 10.1002/ejoc.200500905

M3 - Article

SP - 1672

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

ER -

Vugts DJ, Veum L, Al-Mafraji K, Lemmens RH, Schmitz RF, de Kanter FJJ et al. A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade. European Journal of Organic Chemistry. 2006;1672. https://doi.org/10.1002/ejoc.200500905