Zinc(II)-Catalyzed Synthesis of Propargylamines by Coupling Aldimines and Ketimines with Alkynes
作者:Syeda Aaliya Shehzadi、Aamer Saeed、Filip Lemière、Bert U. W. Maes、Kourosch Abbaspour Tehrani
DOI:10.1002/ejoc.201701567
日期:2018.1.10
Imines derived from unactivated aldehydes or ketones and primary amines or α‐amino acid esters have been shown to undergo a ZnII‐catalyzed reaction with a variety of terminal alkynes to give secondary propargylamines that have tri‐ and tetrasubstituted α‐carbon atoms (from aldimines and ketimines, respectively).
Copper(I)-Catalyzed Ketone, Amine, and Alkyne Coupling for the Synthesis of 2-Alkynylpyrrolidines and -piperidines
作者:Wim E. Van Beek、Joren Van Stappen、Philippe Franck、Kourosch Abbaspour Tehrani
DOI:10.1021/acs.orglett.6b02127
日期:2016.10.7
A Cu(I)-catalyzed coupling of a ω-chloro ketone, a primary amine, and an alkyne is described. This protocol allows for the synthesis of α-quaternary carbons in 2-alkynyl-substituted N-heterocycles. The keystep is the in situ generation of a cyclic ketiminium species, which has enhanced reactivity for alkynylation compared to acyclic ketiminium species.