Alkali–Amide-Catalyzed One-Pot Aminoallylation of Aldehydes with Allylbenzenes
Yuanyun Gu, Yan‐En Wang, Yaqi Yuan, Haodong Xu, Yizhou Lu, Yufei Zhang, Fei Xue, Dan Xiong, Jianyou Mao
Abstract
The deprotonation of allylbenzene was successfully demonstrated with a catalytic alkali amide base (NaN(SiMe 3 ) 2 ). The deprotonated allyl anion could be trapped by in situ generated N -(trimethylsilyl) aldimines to provide value-added homoallylic amines (39 examples, 68–98% yields) in a one-pot manner with excellent liner selectivity. Compared with the previously reported method for the synthesis of homoallylic amines, this method does not need to use the preinstalled protection groups on the imines, which need to be removed after the reaction to obtain the N–H free homoallylic amine derivatives.
Topics & Concepts
CatalysisAmideAlkali metalChemistryOrganic chemistryAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsChemical Synthesis and Reactions