Catalytic asymmetric synthesis of chiral thiohydantoins via the domino cyclization reaction of β,γ-unsaturated α-ketoesters and N,N′-dialkylthiourea

Abstract

The first catalytic asymmetric route to synthesize chiral thiohydantoins containing a quaternary stereogenic center has been established using a chiral phosphoric acid catalyzed domino cyclization reaction of N,N′-dialkyl thioureas with β,γ-unsaturated α-ketoesters. By applying a chiral phosphoric acid catalyst, various chiral thiohydantoins containing a hemiaminal structure were obtained in high yields and excellent enantioselectivities (up to 97% ee) and two C–N bonds could be constructed in this reaction.