Palladium-Catalyzed Dynamic Kinetic Desymmetrization: Enantioselective Construction of Atropisomers with Contiguous
Kaifeng Chen1, Chun-Dong Huang2, Binhong Tan1
1College of Materials and Energy, South China Agricultural University, Guangzhou 510642, Guangdong, China.
Abstract:
We herein report a highly diastereo- and enantioselective palladium-catalyzed dynamic kinetic desymmetrization of heterobicyclic alkenes with heterobiaryl sulfonates. This methodology enables the streamlined construction of complex heterobiaryl atropisomers featuring both an axis of chirality and two contiguous stereocenters. Comprehensive mechanistic investigations, synergistically supported by DFT calculations, firmly establish a dynamic kinetic asymmetric transformation (DYKAT) pathway. Furthermore, the profound utility of these structurally privileged scaffolds is underscored by versatile late-stage diversification, alongside their promising applications as novel chiral organocatalysts and potent antitumor lead candidates.
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