123552-76-1Relevant academic research and scientific papers
α-Benzylation of Ketones by Reaction with Benzylamine. Regioselective Reduction of C-C Double Bonds in Cohjugated Enones
Armesto, Diego,Esteban, Soledad,Horspool, William M.,Martin, Juan-Antonio F.,Martinez-Alcazar, Paz,Perez-Ossorio, Rafael
, p. 751 - 755 (2007/10/02)
Prolonged reaction of some ketones with benzylamine at reflux converts them into α-benzyl derivatives by a route involving Aldol condensation of the related ketimine with benzaldimine followed by exclusive reduction of the resultant C-C double bond.Reduction does not occur when pure benzylamine is used under oxygen-free nitrogen, however the inclusion of a trace of benzaldehyde restores the efficiency of the reaction.Treatment of several ketones in this manner established the scope of the process.When the reaction was extended to the reduction of α,β-unsaturated enones again using benzylamine, reaction times were shorter and the product yield greater.The possibility that the reductive step was an intramolecular 1,5-hydrogen transfer was studied.
