Cu(I)-Catalyzed anti-Selective Aminochlorination of Enones

Significance

In the presence of CuOTf, aromatic α,β-unsaturated ketones can undergo regio- and stereoselective aminochlorination to generateα-amino-β-chloroketones. The reaction is completely regioselective, with stereoselectivities ranging from good to excellent. Only aromatic (E)-β-aryl ketones were explored, no mention is made of aliphatic ketones. Mechanistically, an aziridinium intermediate is proposed, followed by attack at the β-carbon by chloride in an S_N2 manner to generate the products.