Issue 24, 2014

Catalytic enantioselective nucleophilic addition of ynamides to aldehydes

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

Supplementary files

Article information

Article type
Communication
Submitted
17 Jan 2014
Accepted
06 Feb 2014
First published
06 Feb 2014

Chem. Commun., 2014,50, 3151-3154

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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