Rare earth triflates/chlorotrimethylsilane induced activation of triethylamine as a latent acetaldehyde anion: a new synthesis of α,β-unsaturated aldehydes

A synthetic methodology for α,β-unsaturated aldehydes employing rare earth triflate is reported. Activated triethylamine reacts with aldehydes to form two carbon extended aldehydes, which is promoted by a catalytic amount of Yb, Sc, Y, and In(OTf) 3, in the presence of chlorotrimethylsilane. We inve...

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Bibliographic Details
Published in:Tetrahedron letters 2010-01, Vol.51 (3), p.482-484
Main Authors: Kagawa, Natsuko, Sasaki, Yoshiko, Kojima, Hideo, Toyota, Masahiro
Format: Article
Language:English
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Summary:A synthetic methodology for α,β-unsaturated aldehydes employing rare earth triflate is reported. Activated triethylamine reacts with aldehydes to form two carbon extended aldehydes, which is promoted by a catalytic amount of Yb, Sc, Y, and In(OTf) 3, in the presence of chlorotrimethylsilane. We investigated the conditions applicable to aromatic aldehydes as well as heterocyclic compounds as substrates. A deuterium labeling experiment supported our proposed reaction mechanism.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.11.014