Asymmetric Synthesis of N-N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations

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.

Automated summary

N-N axially chiral skeletons play important roles in natural products, pharmaceuticals, and functional materials. A method for asymmetric synthesis of these compounds using phase-transfer catalysis was successfully developed, resulting in high yields and excellent stereoselectivities. The mechanism was further elucidated through density functional theory calculations.