Asymmetric Deoxygenative Alkynylation of Tertiary Amides Enabled by Iridium/Copper Bimetallic Relay Catalysis

A variety of inert tertiary amides have been successfully transformed into synthetically important chiral propargylamines in high yields with good to excellent enantioselectivities via a relayed sequence of Ir catalyzed partial reduction and Cu/GARPHOS catalyzed asymmetric alkynylation with terminal alkynes. The reaction was readily extended to some drug molecules and the transformations of representative products have been demonstrated, thus attesting the practical utilities and the robust nature of the protocol.

Automated summary

Inert tertiary amides have been effectively transformed into chiral propargylamines with high yields and good to excellent enantioselectivities through a relayed sequence of partial reduction and asymmetric alkynylation. The practical utilities and robust nature of this protocol have been demonstrated through the transformations of representative products.