4 + 2] Annulation of δ-Hydroxy/δ-Sulfonamido-α,β-Unsaturated Ketones with Azlactones for Diastereoselective Synthesis of Highly Substituted 3-Amino-δ-Lactones and 3-Amino-δ-Lactams

Abstract

The first base-mediated [4 + 2] annulation of δ-hydroxy-α,β-unsaturated ketones with azlactones has been developed, through which 3,4-disubstituted 3-amino-δ-lactones were obtained in good yields and with excellent diastereoselectivities. This approach was also applied to the [4 + 2] annulation of δ-sulfonamido-α,β-unsaturated ketones, which provided a practical protocol for constructing biologically important 3-amino-δ-lactam frameworks.