Synthesis of Axially Chiral Biaryl‐2‐amines by Pd<sup>II</sup>‐Catalyzed Free‐Amine‐Directed Atroposelective C−H Olefination
Bei‐Bei Zhan, Lei Wang, Jun Luo, Xufeng Lin, Bing‐Feng Shi
Abstract
Abstract 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.
Topics & Concepts
Amine gas treatingCatalysisChemistryCombinatorial chemistryOrganic chemistryMedicinal chemistryAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsSphingolipid Metabolism and Signaling