Pd-Catalyzed Atroposelective C–H Olefination: Diverse Synthesis of Axially Chiral Biaryl-2-carboxylic Acids

Axially chiral carboxylic acids are important motifs in chiral catalysts and ligands. We herein reported the synthesis of axially chiral carboxylic acids via Pd­(II)-catalyzed atroposelective C–H olefination using carboxylic acid as the native directing group. A broad range of axial chiral biaryl-2-...

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Veröffentlicht in:Organic letters 2024-07, Vol.26 (27), p.5670-5675
Hauptverfasser: Jiang, Ao-Lian, Zhou, Gang, Jiang, Bo-Yang, Zhou, Tao, Xu, Xue-Tao, Shi, Bing-Feng
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Sprache:eng
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Zusammenfassung:Axially chiral carboxylic acids are important motifs in chiral catalysts and ligands. We herein reported the synthesis of axially chiral carboxylic acids via Pd­(II)-catalyzed atroposelective C–H olefination using carboxylic acid as the native directing group. A broad range of axial chiral biaryl-2-carboxylic acids were synthesized in good yields with high enantioselectivities (up to 84% yield with 99% ee). Gram-scale reaction and further transformation reactions also provide a platform for synthetic applications of this method.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01656