Catalytic Desymmetrizing Carbonyl–Amine Condensation Reaction to Construct Axially Chiral Diaryl Ethers

Abstract Catalytic desymmetrizing carbonyl–amine condensation (CAC) reactions between prochiral 2,6-diamino diaryl ethers and cyclobutane-1,3-diones have been developed for the highly enantioselective synthesis of axially chiral diaryl ethers in up to 99% ee values. This reaction represents the first application of prochiral aromatic amines in catalytically asymmetric CAC reactions. Control experiments revealed that cyclobutane-1,3-diones showed an obviously higher reactivity and enantioselectivities in these asymmetric CAC reactions.