posted on 2006-03-03, 00:00authored byM. Antonietta Loreto, Antonella Migliorini, P. Antonio Tardella
β-Ketoallylsilanes are synthesized by the Horner−Emmons
reaction starting from novel silylated ketophosphonates and
various aldehydes. The reactions of β-ketoallylsilanes with
NsONHCO2Et and CaO produce α-methylene-N-(ethoxycarbonyl)-β-amino ketones through the ring opening of the
intermediate aziridine, which is favored by the presence of
the trimethylsilyl group. With chiral β-ketoallylsilanes we
obtained a stereoselective amination reaction with a 90%
diastereomeric excess. α-Methylene-N-(ethoxycarbonyl)-β-amino ketones are isolated in 39−60% yields and characterized.