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Issue 24, 2017
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Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts

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Abstract

Herein we report a two-step sequence for the preparation of amides starting from azides and enolisable aldehydes. The reaction proceeded via the formation of triazoline intermediates that were converted into amides via Lewis acid catalysis. Preliminary studies on the preparation of triazolines under chiral phase transfer catalysis are also presented, demonstrating that enantioenriched amides could be prepared from achiral aldehydes in moderate to low enantioselectivity.

Graphical abstract: Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts

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Publication details

The article was received on 30 Mar 2017, accepted on 28 May 2017 and first published on 30 May 2017


Article type: Paper
DOI: 10.1039/C7OB00799J
Citation: Org. Biomol. Chem., 2017,15, 5227-5235
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    Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts

    D. Destro, S. Sanchez, M. Cortigiani and M. F. A. Adamo, Org. Biomol. Chem., 2017, 15, 5227
    DOI: 10.1039/C7OB00799J

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