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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 275-280

GaCl3-catalyzed reactions utilizing isocyanides as a C1 source

Mamoru Tobisu, Masayuki Oshita, Sachiko Yoshioka, Aki Kitajima and Naoto Chatani

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

Abstract: Two GaCl3-catalyzed reactions, which utilize isocyanides as a one-carbon unit, are described: a [4+1] cycloaddition of α,β-unsaturated carbonyl compounds with isocyanides, and an insertion reaction of isocyanides into a C-O bond of ketals and acetals. The relatively low affinity of GaCl3 toward heteroatoms enables the successful catalysis.