Asymmetric Synthesis of Propargylic alfa-Chiral Tertiary Amines by Reductive Alkynylation of Tertiary Amides Using Ir/Cu Tandem Catalysis

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Abstract

The development of an asymmetric protocol for the reductive alkynylation of amides to access important alfa-chiral tertiary propargylic amines is reported using tandem Ir-catalyzed hydrosilylation/enantioselective Cu-catalyzed alkynylation. The reaction utilizes a Cu/PyBox catalyst system in the alkynylation step to achieve asymmetry and affords excellent yields with moderate to good levels of enantiocontrol while employing low Ir-catalyst loadings (0.5 mol %).

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Supplementary material

Supporting Information
Procedures and compound characterization.