α-Alkylation of Mono-Carbonyl Compounds with N-Allylamines through Cooperative Actions of Lewis Acids and a Bronsted Base

We present a strategy for the union of N-allylamines and carbonyl compounds by the concerted action of B(C6F5)(3) and a N-based Bronsted base under redox-neutral conditions. The reaction of in situ generated conjugated iminium ions and enolates affords & delta;-aminocarbonyl compounds without waste generation. Furthermore, we describe that the cooperative action of B(C6F5)(3), a chiral Zn-based complex, and an amine facilitates the stereoselective reaction of a glycinate Schiff base ester and an N-allylamine to afford an & alpha;-substituted & alpha;-amino ester.

Automated summary

We propose a method for the combination of N-allylamines and carbonyl compounds through the concerted action of B(C6F5)(3) and a N-based Bronsted base under redox-neutral conditions. By the reaction of in situ generated conjugated iminium ions and enolates, & delta;-aminocarbonyl compounds are obtained without waste generation. Furthermore, the cooperative action of B(C6F5)(3), a chiral Zn-based complex, and an amine enables the stereoselective reaction of a glycinate Schiff base ester and an N-allylamine to yield an & alpha;-substituted & alpha;-amino ester.