N-Heterocyclic carbene-catalyzed cyclotetramerization of acrylates.
N-Heterocyclic carbenes (NHCs) were found to catalyze the unprecedented cyclotetramerization of acrylates, producing the trisubstituted cyclopentenones in moderate yields. The proton or deuterium adducts of the deoxy-Breslow intermediate derived from NHC and two molecules of methyl acrylate were obtained. A reaction mechanism involving the new umpolung/cyclization sequence is proposed.
Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho , Showa-ku, Nagoya 466-8555, Japan.
Shin-ichi
S
Matsuoka
Shoko
S
Namera
Atsushi
A
Washio
Koji
K
Takagi
Masato
M
Suzuki