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Catalytic Enantioselective Silylation for Simultaneous Axial and Central Chirality in Diaryl Ethers
Han Cai1, Yang-Zi Liu1, Wei-Ping Deng1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China.
Abstract:
Axially chiral diaryl ethers represent a distinctive class of atropisomers wherein rotation about the C-O bond is restricted. Efficient methods for accessing such architectures remain limited. Herein, we report a copper-catalyzed enantioselective silylation of 2-aryloxyisophthalaldehydes using an N-heterocyclic carbene chiral ligand and an Si-B pronucleophile. This approach concurrently establishes both central and axial chirality with high enantioselectivity and diastereoselectivity (up to 95:5 er, >20:1 dr). The resulting axially and centrally chiral products display excellent thermal stability and can be further elaborated into valuable diaryl ether derivatives with minimal erosion of enantiopurity.
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