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Synthesis of Axially Chiral Biaryl‐2‐amines by Pd II ‐Catalyzed Free‐Amine‐Directed Atroposelective C−H Olefination
Author(s) -
Zhan BeiBei,
Wang Lei,
Luo Jun,
Lin XuFeng,
Shi BingFeng
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915674
Subject(s) - chemistry , amine gas treating , axial chirality , phosphoric acid , catalysis , combinatorial chemistry , axial symmetry , ligand (biochemistry) , organic chemistry , enantioselective synthesis , biochemistry , receptor , structural engineering , engineering
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.