One-Pot Construction of Diverse ß-Lactam Scaffolds via the Green Oxidation of Amines and Its Application to the Diastereoselective Synthesis of ß-Amino Acids.

ABSTRACT

In this study, a simple one-pot construction of ß-lactam scaffolds was successfully achieved via 4,6-dihydroxysalicylic acid-catalyzed organocatalytic oxidation of amines to imines using molecular oxygen. Although some imines are highly unstable and difficult to isolate by conventional methods, the organocatalytic oxidation of amines described herein, followed by their direct reaction with acyl chlorides in the presence of a base, afforded a series of new ß-lactam derivatives with excellent cis selectivity, which could not be synthesized and isolated by previously reported methods. Thus, this one-pot protocol will be one of the powerful methods applicable to the synthesis of various potential drug candidates and functional molecules. Furthermore, the subsequent hydrolysis of these ß-lactams successfully afforded the corresponding ß-amino acids as almost single diastereomers in up to 99% yields.