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

doi:10.1002/ejoc.200500905

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

^*Corresponding author for this work

Delft University of Technology
Vrije Universiteit Amsterdam

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.

Original language	English
Pages (from-to)	1672-1677
Number of pages	6
Journal	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.200500905
Publication status	Published - 27 Mar 2006

Keywords

Hydroxynitrile lyase
Oxidation
Oxynitrilase
TEMPO

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title = "A mild chemo-enzymatic oxidation-hydrocyanation protocol",

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.",

keywords = "Hydroxynitrile lyase, Oxidation, Oxynitrilase, TEMPO",

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

year = "2006",

month = mar,

day = "27",

doi = "10.1002/ejoc.200500905",

language = "English",

pages = "1672--1677",

journal = "EUROPEAN JOURNAL OF ORGANIC CHEMISTRY",

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publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - A mild chemo-enzymatic oxidation-hydrocyanation protocol

AU - Vugts, Danielle J.

AU - Veum, Lars

AU - Al-Mafraji, Kanar

AU - Lemmens, Renske

AU - Schmitz, Rob F.

AU - De Kanter, Frans J.J.

AU - Groen, Marinus B.

AU - Hanefeld, Ulf

AU - Orru, Romano V.A.

PY - 2006/3/27

Y1 - 2006/3/27

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.

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.

KW - Hydroxynitrile lyase

KW - Oxidation

KW - Oxynitrilase

KW - TEMPO

UR - https://www.scopus.com/pages/publications/33645516788

U2 - 10.1002/ejoc.200500905

DO - 10.1002/ejoc.200500905

M3 - Article

SN - 1434-193X

SP - 1672

EP - 1677

JO - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

IS - 7

ER -

A mild chemo-enzymatic oxidation-hydrocyanation protocol

Abstract

Keywords

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