Issue 7, 2015

AlCl3-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides

Abstract

The inexpensive Lewis acid AlCl3 was found to be an efficient catalyst for the O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and alcohols. Instead of carboxylic acid in the classical Passerini reaction, alcohols performed both as the solvent and substrate nicely to afford α-alkoxy-amide products in good yield (up to 91%). This method provides practical access for functional α-alkoxy-β,γ-enamide derivatives.

Graphical abstract: AlCl3-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides

Supplementary files

Article information

Article type
Research Article
Submitted
02 Apr 2015
Accepted
28 Apr 2015
First published
30 Apr 2015

Org. Chem. Front., 2015,2, 815-818

Author version available

AlCl3-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides

L. Lyu, H. Xie, H. Mu, Q. He, Z. Bian and J. Wang, Org. Chem. Front., 2015, 2, 815 DOI: 10.1039/C5QO00106D

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