Organocatalytic Multicomponent Synthesis of α/β‐Dipeptide Derivatives

A straightforward multicomponent Knoevenagel‐aza‐Michael‐cyclocondensation reaction involving readily available hydroxamic acid‐derived from naturally occurring α‐amino acids allows a diversity‐oriented synthesis of novel isoxazolidin‐5‐ones possessing an N‐protected α‐amino acid pendant with good to high diastereoselectivities thanks to a match effect with a chiral organocatalyst. These diversely substituted heterocycles, easily isolated as a single diastereoisomer, proved to be versatile platforms for the formation of an array of α/β‐dipeptide fragments. The diversity: A straightforward organocatalyzed multicomponent reaction (MCR) involving readily available hydroxamic acids‐derived from naturally occurring α‐amino acids (αAA) allows a stereoselective and diversity‐oriented synthesis of novel isoxazolidin‐5‐ones as versatile platforms for the elaboration of α/β‐dipeptide fragments.