Asymmetric Synthesis of N–N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations
Ming Pan, Yingbo Shao, Qun Zhao, Xin Li
Abstract
N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. Density functional theory calculations provide insight into the mechanism.
Topics & Concepts
Axial symmetryChemistryCatalysisCombinatorial chemistryAxial chiralityDensity functional theoryPhase (matter)Computational chemistryQuinazolinoneStereochemistryEnantioselective synthesisOrganic chemistryEngineeringStructural engineeringAxial and Atropisomeric Chirality SynthesisQuinazolinone synthesis and applicationsMolecular spectroscopy and chirality