C-N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α-Oxytosylation of Ketones

A simple synthesis of a library of novel C-N axially chiral iodoarenes is achieved in a three-step synthesis from commercially available aniline derivatives. C-N axial chiral iodine reagents are rarely investigated in the hypervalent iodine arena. The potential of the novel chiral iodoarenes as organocatalysts for stereoselective oxidative transformations is assessed using the well explored, but challenging stereoselective alpha-oxytosylation of ketones. All investigated reagents catalyse the stereoselective oxidation of propiophenone to the corresponding chiral alpha-oxytosylated products with good stereochemical control. Using the optimised reaction conditions a wide range of products was obtained in generally good to excellent yields and with good enantioselectivities.

Automated summary

A library of novel C-N axially chiral iodoarenes was successfully synthesized from commercially available aniline derivatives in a three-step synthesis. These novel chiral iodoarenes were found to have potential as organocatalysts for stereoselective oxidative transformations, with good stereochemical control observed in the oxidation of propiophenone.