Catalytic Enantioselective Silylation for Simultaneous Axial and Central Chirality in Diaryl Ethers
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.
Fields of Study & Subjects
Axial and Atropisomeric Chirality Synthesis
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Asymmetric Synthesis and Catalysis
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 16
- Pages
- 5669–5679
- Publication date
- 10 April 2026
- Language
- EN