Copper(I)-Catalyzed Ketone, Amine, and Alkyne Coupling for the Synthesis of 2-Alkynylpyrrolidines and -piperidines.
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 key step is the in situ generation of a cyclic ketiminium species, which has enhanced reactivity for alkynylation compared to acyclic ketiminium species.
Organic Synthesis, Department of Chemistry, University of Antwerp , Groenenborgerlaan 171, B-2020 Antwerp, Belgium.
Wim E
WE
Van Beek
Organic Synthesis, Department of Chemistry, University of Antwerp , Groenenborgerlaan 171, B-2020 Antwerp, Belgium.
Joren
J
Van Stappen
Organic Synthesis, Department of Chemistry, University of Antwerp , Groenenborgerlaan 171, B-2020 Antwerp, Belgium.
Philippe
P
Franck
Organic Synthesis, Department of Chemistry, University of Antwerp , Groenenborgerlaan 171, B-2020 Antwerp, Belgium.
Kourosch
K
Abbaspour Tehrani