1. Synthetic applications of aziridines: New approaches to the development of asymmetric catalysts. 2. Studies of new reactivity fo p-tolylsulfinayl amides towards olefins

Abstract

The new N,N-ligands have been synthesized. It was shown that Cu(I) coordinates to the ligands. Enantiomerically pure forms of this ligand were obtained and applied to the cyclopropanation reaction, where the copper catalyst revealed unexpectedly high diastereoselectivity in comparison with the ruthenium catalyst. Observed diastereoselectivities are superior to the known copper catalyzed cyclopropanation. New reactivity of the sulfinyl amide was discovered. Reaction between alkenes and sulfinyl amides in the presence of POCl3 was found to proceed with the formation of β-chlorosulfides. Optimized reaction conditions were applied to a wide range of substrates. In the absence of nucleophile under Lewis acid conditions p-tolylsulfinyl amide reacted with α-methylstyrene with the formation of allylsulfoxide. This chemistry provides a reasonable alternative to currently used oxidative methods of sulfoxides synthesis.