Asymmetric synthesis of β-aryl-β-trifluoromethyl-β-aminoarones via Mannich-type reactions of ketone enolates with chiral aryl CF3-substituted N-tert-butanesulfinyl ketimines

A method for the preparation of chiral β-aryl-β-trifluoromethyl-β-aminoarones has been developed involving the Mannich-type reactions of ketone-derivative enolates with chiral aryl CF3-substituted N-tert-butanesulfinyl ketimines. This method tolerates a wide of aromatic ketones, giving the products in moderate to excellent yields (up to 91%) with good diastereoselectiveties (up to 93:7 dr). Acidic cleavage of the tert-butanesulfinyl group gave optically pure β-aryl-β-trifluoromethyl-β-aminoarones in excellent yields (up to 98%), which can be further transformed into CF3-substituted aziridine derivatives.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide