期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 9, 页码 3568-3572出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915674
关键词
atroposelectivity; biaryl-2-amines; C-H olefination; chiral spiro phosphoric acids; palladium
资金
- NSFC [21925109, 21772170, 21822303, 21772020]
- Outstanding Young Talents of Zhejiang Province High-level Personnel of Special Support [ZJWR0108]
- Fundamental Research Funds for the Central Universities [2018XZZX001-02]
- Zhejiang Provincial NSFC [LR17B020001]
A simple and ubiquitously present group, free amine, is used as a directing group to synthesize axially chiral biaryl compounds by Pd-II-catalyzed atroposelective C-H olefination. A broad range of axially chiral biaryl-2-amines can be obtained in good yields with high enantioselectivities (up to 97 % ee). Chiral spiro phosphoric acid (SPA) proved to be an efficient ligand and the loading could be reduced to 1 mol % without erosion of enantiocontrol in gram-scale synthesis. The resulting axially chiral biaryl-2-amines also provide a platform for the synthesis of a set of chiral ligands.
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