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Issue 77, 2015
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Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres

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Abstract

An intermolecular tandem reaction for the rapid build-up of densely functionalised α-alkoxy-β-oxo-esters has been developed. This novel process applies the easy to handle trimethyl orthoformate as a C1-building block in the rhodium(II)-catalysed alkoxylation/acetalization of donor–acceptor substituted diazo compounds. The concomitant C–O/C–C bond formation reaction gives products with unique quaternary carbon centers, substituted by groups of different oxidation level (ester, protected aldehyde and alkoxide).

Graphical abstract: Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres

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Publication details

The article was received on 11 May 2015, accepted on 11 Aug 2015 and first published on 11 Aug 2015


Article type: Communication
DOI: 10.1039/C5CC03903G
Chem. Commun., 2015,51, 14505-14508

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    Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres

    J. Pospech, A. J. J. Lennox and M. Beller, Chem. Commun., 2015, 51, 14505
    DOI: 10.1039/C5CC03903G

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