Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions with Kinetic Resolution

Kinetic resolution is an efficient and widely used asymmetric organic synthesis strategy, which can transform racemic compounds into highly optically active building blocks. It is quite an important part of modern asymmetric synthesis. Although it has long been known as a common method to gain enantioenriched raw material, kinetic resolution processes involving asymmetric catalysis often show poor resolution efficiency and limited substrates scope in practice, which greatly hinder the development of this strategy. It is not until the past two decades, with the rapid development of chiral ligands and catalysts in the field of asymmetric catalysis, that kinetic resolution strategy has been increasingly applied in the efficient separation of racemic substrates to provide versatile chiral molecules with excellent optical purity. Since the strategy of kinetic resolution was first successfully employed in the catalytic asymmetric 1,3-dipolar cycloadditions with azomethine imines in 2005, studies on 1,3-dipolar cycloadditions with efficient kinetic resolution to achieve chiral N-heterocyclic compounds or highly enantioselective fragments have been well developed. The recent progress of kinetic resolution strategy in catalytic asymmetric 1,3-dipolar cycloaddition reactions involving azomethine imines and azomethine ylides is summarized according to the different azomethine 1,3-dipoles involved, and the related limitations and development prospects are also discussed.

Automated summary

Kinetic resolution is an important strategy in asymmetric organic synthesis, which converts racemic compounds into highly optically active building blocks. However, in practice, kinetic resolution processes often have poor resolution efficiency and limited substrate scope. Recent developments in chiral ligands and catalysts have enabled the efficient separation of racemic substrates using the kinetic resolution strategy, resulting in versatile chiral molecules with excellent optical purity.