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

✍ Scribed by Natsuko Kagawa; Yoshiko Sasaki; Hideo Kojima; Masahiro Toyota

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 307 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.11.014

✦ Synopsis

A synthetic methodology for a,b-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.