Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202216534
Keywords
Asymmetric Catalysis; Axial Chirality; Dynamic Kinetic Resolution; Ethers; Phosphoric Acids
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This paper presents a dynamic kinetic resolution method for the synthesis of axially chiral diaryl ethers. By using a Bronsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction, the desired diaryl ethers could be obtained in moderate to good chemical yields (up to 79%) and high enantioselectivities (up to 95% ee) under standard reaction conditions. These structural motifs are interesting precursors for further transformations and may have potential applications in the synthesis of chiral ligands or catalysts.
Diaryl ethers are widespread in biologically active compounds, ligands and catalysts. It is known that the diaryl ether skeleton may exhibit atropisomerism when both aryl rings are unsymmetrically substituted with bulky groups. Despite recent advances, only very few catalytic asymmetric methods have been developed to construct such axially chiral compounds. We describe herein a dynamic kinetic resolution approach to axially chiral diaryl ethers via a Bronsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction of dicarbaldehydes with anilines. The desired diaryl ethers could be obtained in moderate to good chemical yields (up to 79 %) and high enantioselectivities (up to 95 % ee) under standard reaction conditions. Such structural motifs are interesting precursors for further transformations and may have potential applications in the synthesis of chiral ligands or catalysts.
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