Highly Diastereo- and Enantioselective Copper-Catalyzed Dipropargylic Amination to Access Bispropargylic Diamines

Herein we described the diastereo- and enantioselective copper-catalyzed dipropargylic amination between propargylic acetates and diamines. The reaction features readily available substrates and broad functional group compatibility, as well as mild reaction conditions. Various synthetically valuable chiral bispropargylic diamines can be furnished in high yields with good to excellent diastereo- and enantioselectivities (up to 98% yield, >95 : 5 dr, >99% ee). The products further can be transformed into chiral bispropargylic diamines containing two internal alkyne groups and novel potential C2-symmetric chiral tetraaza ligands without any loss of diastereo- and enantioselectivity.