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.

doi:10.1002/ejoc.200500905

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 Journal › Article › Academic › peer-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 language	English
Pages (from-to)	1672
Journal	European Journal of Organic Chemistry
DOIs	https://doi.org/10.1002/ejoc.200500905
Publication status	Published - 2006

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title = "A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade",

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. {\textcopyright} 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.",

year = "2006",

doi = "10.1002/ejoc.200500905",

language = "English",

pages = "1672",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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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.

U2 - 10.1002/ejoc.200500905

DO - 10.1002/ejoc.200500905

M3 - Article

SN - 1434-193X

SP - 1672

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

A Mild Chemo-Enzymatic Oxidation-Hydrocyanation Cascade

Abstract

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