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Catalyst‐Controlled Wacker‐Type Oxidation of Protected Allylic Amines
Journal article   Open access  Peer reviewed

Catalyst‐Controlled Wacker‐Type Oxidation of Protected Allylic Amines

Brian W Michel, Jessica R McCombs, Andrea Winkler and Matthew S Sigman
Angewandte Chemie (International ed.), Vol.49(40), pp.7312-7315
09/24/2010
PMCID: PMC3035046
PMID: 20799310

Abstract

oxidation palladium complexes homogeneous catalysis Wacker‐type reaction catalyst control
On the contrary: Utilizing the [Pd(quinox)]–TBHP catalyst system, protected allylic amines were oxidized with high selectivity for the methyl ketone product. This is contrary to the results obtained by the substrate‐controlled Tsuji–Wacker oxidation, which highlights the catalyst‐controlled system presented here (see scheme). A variety of N‐protecting groups undergo selective oxidation with high ketone selectivity. TBHP=tert‐butylhydroperoxide.
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https://doi.org/10.1002/anie.201004156View
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