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Issue 48, 2016
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Highly efficient synthesis of functionalized α-oxyketones via Weinreb amides homologation with α-oxygenated organolithiums

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Abstract

An efficient, chemoselective homologation of Weinreb amides to the corresponding variously substituted α-oxyketones has been developed via the addition of lithiated α-oxygenated species. This one-step, experimentally easy, high yielding protocol is amenable not only for accessing simple α-oxyketones but also for more complex substituted ones ranging from primary and secondary alkyl-type to aromatic ones. Full delivery of the stereochemical information contained in the starting materials is observed through both the employment of enantioenriched Weinreb amides and optically active organolithium species.

Graphical abstract: Highly efficient synthesis of functionalized α-oxyketones via Weinreb amides homologation with α-oxygenated organolithiums

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Publication details

The article was received on 27 Apr 2016, accepted on 18 May 2016 and first published on 19 May 2016


Article type: Communication
DOI: 10.1039/C6CC03532A
Citation: Chem. Commun., 2016,52, 7584-7587
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    Highly efficient synthesis of functionalized α-oxyketones via Weinreb amides homologation with α-oxygenated organolithiums

    V. Pace, I. Murgia, S. Westermayer, T. Langer and W. Holzer, Chem. Commun., 2016, 52, 7584
    DOI: 10.1039/C6CC03532A

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