793733-49-0Relevant academic research and scientific papers
Ruthenium-catalyzed reaction of α,β-unsaturated imines with carbon monoxide and alkenes leading to β,γ-unsaturated γ-butyrolactams: Involvement of direct carbonylation at olefinic C-H bonds as a key step
Chatani, Naoto,Kamitani, Akihito,Murai, Shinji
, p. 7014 - 7018 (2007/10/03)
The reaction of α,β-unsaturated imines with CO and alkenes in the presence of Ru3(CO)12 as a catalyst results in a three-component coupling reaction that gives α,α-disubstituted β,γ-unsaturated γ-butyrolactams. The reaction proceeds via a two-step sequence involving the initial formation of ketone derivatives by catalytic carbonylation at the β-olefinic C-H bonds of α,β-unsaturated imines, followed by the (uncatalyzed) intramolecular nucleophilic attack of the imine nitrogen on the ketonic carbon to generate a tetrahedral intermediate, which then undergoes a 1,2-ethyl migration. The reaction of a cyclic unsaturated imine, derived from the reaction of (1R)-(-)-myrtenal with tertbutylamine, gives a β-aminocyclopentene derivative, which is formed by an aldol-type condensation of the initially formed ketone, indicating the initial formation of ethyl ketone.
