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.