title: Ynolate chemistry. Reaction of a silylynolate with aziridines leading to gamma-lactams.
abstract: A silylynolate, generated via the carbonylation of lithium silyldiazomethane, was reacted with N-tosyl aziridines to produce various five-membered lactams in good yields. The key step of this reaction involves the ring-opening ketenylation of aziridines by the silylynolate. The reaction proceeded in a highly stereoselective manner, and ketenylation took place at the less hindered carbon. When treated with aldehydes prior to protonation, the alpha-silylated lactam enolates gave alpha-vinylidene gamma-lactams. These reactions represent a unique path to the generation of and for controlling the reactivity of a rare class of reactive intermediates, namely, acyllithium derivatives and ynolates.
authors: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
authors: K
authors: K
authors: Iwamoto
authors: M
authors: M
authors: Kojima
authors: N
authors: N
authors: Chatani
authors: S
authors: S
authors: Murai