Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides
Toolika Agrawal, Robert T. Martin, Stephen F. Collins, Zachary Wilhelm, Mytia D. Edwards, Osvaldo Gutiérrez, Joshua D. Sieber
Abstract
-alkyl substituted aldimines to access chiral 1,2-diamino synthons as single stereoisomers in high yields. The method shows broad reaction scope and high diastereoselectivity and can be easily scaled using standard Schlenk techniques. Mechanistic investigations by density functional theory calculations identified the mechanism and origin of stereoselectivity. In particular, the addition to the imine was shown to be reversible, which has implications toward development of catalyst-controlled stereoselective variants of the identified reductive coupling of imines and allenamides.
Topics & Concepts
StereoselectivityChemistryImineSynthonCombinatorial chemistryAldimineCatalysisEnantioselective synthesisDiamineReductive eliminationOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions