A highly α-regioselective In(OTf)3-catalyzed N-nucleophilic substitution of cyclic Baylis-Hillman adducts with aromatic amines

The highly α-regioselective N-nucleophilic substitution of B-H adducts bearing five (1a-f) or six-membered ring (5a-e) moieties with aromatic amines (2a-e) was developed under the catalysis of In(OTf)3 (10 mol%). During the reaction the allylic rearrangement from γ-product to α-product occurred, resulting in thermodynamically stable α-product predominately.