Catalytic Enantioselective Synthesis of Amino Skipped Diynes

The Cu-catalyzed synthesis of nonracemic 3-amino skipped diynes via an enantiodetermining C–C bond formation is described using StackPhos as ligand. Despite challenging issues of reactivity and stereoselectivity inherent to these chiral skipped diynes, the reaction tolerates an extremely broad substrate scope with respect to all components and provides the title compounds in excellent enantiomeric excess. The alkyne moieties are demonstrated here to be useful synthetic handles, and 3-amino skipped diynes are convenient building blocks for enantioselective synthesis.