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Mechanistic insights into transition metal-catalysed oxidation of a hydroxamic acid with in situ Diels-Alder trapping of the acyl nitroso derivative

Lookup NU author(s): Professor Allen Wright

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Abstract

New insights into the mechanism for the transition metal-mediated oxidation of hydroxamic acids to give intermediate acyl nitroso species, with subsequent hetero-Diels-Alder trapping are presented. The activation of triphenylphosphine-ligated ruthenium-salen complexes is examined, and evidence is presented for the ruthenium-oxo species which are involved in the oxidative process of the hydroxamic acid. The observation of the lack of asymmetric induction involved in the intermolecular cycloaddition process involving the intermediate acyl nitrsoso species is explained, with the aid of comparing the ruthenium-salen-based systems with nitrosotoluene, and copper(I)/copper(II) BINAP-based catalysis of nitrosopyridine complexes. This study demonstrates the importance of secondary coordination to achieve asymmetric induction in nitroso-Diels-Alder reactions.

Publication metadata

Author(s): Howard JAK, Ilyashenko G, Sparkes HA, Whiting A, Wright AR

Publication type: Article

Publication status: Published

Journal: Advanced Synthesis & Catalysis

Year: 2008

Volume: 350

Issue: 6

Pages: 869-882

ISSN (print): 1615-4150

ISSN (electronic): 1615-4169

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/adsc.200700568

DOI: 10.1002/adsc.200700568

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