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Regioselective [3+3] annulation of alkynyl ketimines with α‐cyano ketones for the synthesis of polysubstituted 4H‐pyran derivatives with a quaternary CF3‐containing center has been realized by using Cu(OAc)2 as the catalyst. The novel strategy tolerates a wide range of α‐CF3 alkynyl ketimines and α‐cyano ketones with both aryl and alkyl substitutents. A preliminary asymmetric synthesis of chiral product...