The Aldol Reaction of α‐Ketoamide with α,β‐Unsaturated Ketone in KOH Aqueous Medium

Abstract

Herein, we report for the first time the aldol reaction of a wide range of α‐ketoamide with α,β‐unsaturated ketone via the activation of potassium hydroxide in aqueous medium. The protocol provides a straightforward and atom‐efficient strategy for the synthesis of a new family of multifunctional α‐hydroxy amides contain α,β‐unsaturated ketone group from easily accessible substituted α‐ketoamide and α,β‐unsaturated ketone. The reaction features mild reaction conditions, green solvent, one of which is quaternary carbon substitution. The method can accommodate various substituents and substitution patterns, afford the products up to 95 % yields.

Highly regioselective synthesis of lactamsviacascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst

“…Numerous natural products and pharmacologically active compounds contain the structure of the bicyclic lactams with cyclopentanone scaffold, showing the importance of this structural motif in synthetic organic chemistry. 6 Based on our previous research on ketoamides, 48,49 herein, we presented a novel high region-, diastereoselective and atom economical to synthesis of bicyclic lactams via the cascade reaction of aldol-Michael addition on the b and g-positions of cyclopentenone with ketoamides by DBU catalyzed (Scheme 1).…”