Enantioselective Construction of C–C Axially Chiral Quinazolinones via Chirality Exchange and Phase-Transfer Catalysis
Zeng Gao, Jinlong Qian, Huameng Yang, Jinlong Zhang, Gaoxi Jiang
Abstract
A family of axially chiral quinazolinone-based heterobiaryls were constructed with high levels of enantiocontrol (up to 94% ee). Convergently, three different synthetic methods have been realized to prepare these valuable compounds including central-to-axial chirality transfer, dynamic kinetic resolution, and phase-transfer catalysis. Importantly, novel P,N-ligands with a π-π stacking can be derived from heterobiaryls by chirality exchange strategy or synthesized directly from complementary phase-transfer catalysis by using the inexpensive chiral quaternary ammonium salt.
Topics & Concepts
Enantioselective synthesisChirality (physics)ChemistryKinetic resolutionCatalysisStackingAxial chiralityQuinazolinoneAxial symmetryCombinatorial chemistryPhase (matter)StereochemistryOrganic chemistryPhysicsChiral anomalyNambu–Jona-Lasinio modelQuantum mechanicsFermionAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling