Kinetic Resolution of Sulfinamides via Asymmetric N-Allylic Alkylation

An efficient kinetic resolution of sulfinamides via an asymmetric N-allylic alkylation reaction was realized using hydroquinine as a catalyst under mild conditions. The kinetic resolution of a range of Morita-Baylis-Hillman adducts and N-aryl tert-butylsulfinamides was highly effective. In addition, the synthetic utility of the protocol was demonstrated by a scaled-up reaction. Density functional theory calculations provide convincing evidence for the interpretation of stereoselection.

Automated summary

Efficient kinetic resolution of sulfinamides was achieved via an asymmetric N-allylic alkylation using hydroquinine as a catalyst under mild conditions. The method showed high effectiveness in resolving a range of Morita-Baylis-Hillman adducts and N-aryl tert-butylsulfinamides, with the synthetic utility of the protocol demonstrated through scaled-up reactions. Density functional theory calculations provided convincing evidence for the interpretation of stereoselection.