Chiral bispropargylic diamines have important application value in synthetic chemistry. Copper-catalyzed dipropargylic amination could furnish various chiral bispropargylic diamines in high yields with good to excellent diastereo- and enantioselectivities under mild reaction conditions. The products further can be transformed into other promising compounds without any loss of diastereo- and enantioselectivity.
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.Zum Volltext