Synthesis of Axially Chiral Diaryl Ethers via NHCs-Catalyzed Desymmetrization Followed By Kinetic Resolution

Axially chiral diaryl ethers bearing two potential axes found unique applications in bioactive molecules. However, only very few catalytic methods have been developed to construct structurally diverse diaryl ethers. We herein describe an NHC-catalyzed atroposelective esterification of biaryl dialdehydes leading to the synthesis of flexible axially chiral diaryl ethers. Mechanistic studies indicate that coupling proceeds through NHC-catalyzed desymmetrization of the dialdehydes and matched kinetic resolution. This protocol features excellent enantioselectivity, mild conditions, good functional-group tolerance, and applicability to late-stage functionalization and provides a modular platform for the synthesis of axially chiral diaryl ethers. and their derivatives.