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Issue 24, 2014
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Catalytic enantioselective nucleophilic addition of ynamides to aldehydes

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Abstract

The first catalytic asymmetric addition of ynamides to aliphatic and aromatic aldehydes is described. This reaction provides unprecedented access to a diverse family of N-substituted propargylic alcohols that are obtained in high yield and ee in the presence of 10 mol% of zinc triflate and N-methylephedrine. The use of apolar solvent mixtures is essential to avoid product racemization and to optimize ee's without compromising conversion.

Graphical abstract: Catalytic enantioselective nucleophilic addition of ynamides to aldehydes

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Publication details

The article was received on 17 Jan 2014, accepted on 06 Feb 2014 and first published on 06 Feb 2014


Article type: Communication
DOI: 10.1039/C4CC00394B
Chem. Commun., 2014,50, 3151-3154

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    Catalytic enantioselective nucleophilic addition of ynamides to aldehydes

    A. M. Cook and C. Wolf, Chem. Commun., 2014, 50, 3151
    DOI: 10.1039/C4CC00394B

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