Enantioselective addition of phenyl and alkyl acetylenes to imines catalyzed by chiral Cu(I) complexes

The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups

“…civ,cv The use of 1-decyne was tolerated in the presence of bis-imine 133 to furnish the corresponding propargyl amine 134c in 91% yield and 73% ee (Scheme 29). This represents the first example of an enantioselective addition of an aliphatic alkyne to an imine.…”

Recent Developments in Asymmetric Alkynylation of Imines

“…In the search for new chiral catalysts for the enantioselective alkynylation of imines Benaglia et al have examined the copper(I) triflate complexes of a series of bis-imines (121-127) with C 2 -symmetry (Scheme 48) [51]. All ligands were able to promote the reaction between phenylacetylene and imine 82 at rt, with the exception of ligand 127, for which, the presence of four coordinating atoms rendered the Cu complex catalytically inactive.…”

Unprecedented one-pot multicomponent synthesis of propargylamines using Amberlyst A-21 supported CuI under solvent-free conditions

“…19,20 The three-component coupling of aldehydes, amines, and alkynes is an example of MCR and has received much attention in recent years. [28][29][30][31][32][33][34] Nevertheless, the C-H activation of the terminal alkyne bond has mostly been studied using copper as the catalyst. [28][29][30][31][32][33][34] Nevertheless, the C-H activation of the terminal alkyne bond has mostly been studied using copper as the catalyst.…”