Alkali-Amide-Catalyzed One-Pot Aminoallylation of Aldehydes with Allylbenzenes

The deprotonation of allylbenzene was successfully demonstratedwith a catalytic alkali amide base (NaN-(SiMe3)(2)). The deprotonated allyl anion could be trapped by in situ generated N-(trimethylsilyl) aldimines to provide value-added homoallylicamines (39 examples, 68-98% yields) in a one-pot manner withexcellent liner selectivity. Compared with the previously reportedmethod for the synthesis of homoallylic amines, this method does notneed to use the preinstalled protection groups on the imines, whichneed to be removed after the reaction to obtain the N-H freehomoallylic amine derivatives.

Automated summary

The deprotonation of allylbenzene was achieved using a catalytic alkali amide base, and the resulting allyl anion was trapped by N-(trimethylsilyl) aldimines to synthesize homoallylic amines. This one-pot method provided value-added products with excellent selectivity without the need for protection groups on the imines.