Asymmetric Synthesis of Propargylic α-Stereogenic Tertiary Amines by Reductive Alkynylation of Tertiary Amides Using Ir/Cu Tandem Catalysis
Toolika Agrawal, Kimberly D. Perez-Morales, Jermaine A. Cort, Joshua D. Sieber
Abstract
The development of an asymmetric protocol for the reductive alkynylation of amides to access important α-stereogenic tertiary propargylic amines is reported using a 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 %).
Topics & Concepts
StereocenterAlkynylationChemistryEnantioselective synthesisCatalysisTandemHydrosilylationCombinatorial chemistryCascade reactionOrganic chemistryComposite materialMaterials scienceAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis