Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 275-280
doi:10.1351/pac200678020275
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.
Keywords: acetals; GaCl3; isocyanide; ketals; unsaturated ketones.
*Pure Appl. Chem. 78, 197-523. An issue of reviews and research papers based on lectures presented at the 13th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), Geneva, Switzerland, 17-21 July 2005.