Organocatalytic Multicomponent Synthesis of α/β‐Dipeptide Derivatives Article - Mars 2020

Thomas Martzel, Julien Annibaletto, Pierre Millet, Etienne Pair, Morgane Sanselme, Sylvain Oudeyer, Vincent Levacher, Jean-François Brière

Thomas Martzel, Julien Annibaletto, Pierre Millet, Etienne Pair, Morgane Sanselme, Sylvain Oudeyer, Vincent Levacher, Jean-François Brière, « Organocatalytic Multicomponent Synthesis of α/β‐Dipeptide Derivatives  », Chemistry - A European Journal, mars 2020. ISSN 0947-6539

Abstract

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.

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