Catalysis

Intramolecular force

Enantioselective synthesis

Phase (matter)

Engineering

Density functional theory

Axial chirality

Stereochemistry

Combinatorial chemistry

Organic chemistry

Axial symmetry

Computational chemistry

Quinazolinone

Structural engineering

Chemistry

Organic Letters

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.

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