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
2012
Abstract 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 CF 3 -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 CF 3 -substituted aziridine derivatives.
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