6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis?

RSC Advances Pub Date: 2021-07-14 DOI: 10.1039/D1RA04651A

Abstract

It was found that 6-halo-2-pyridones catalysed ester aminolysis in which not only reactive aryl esters but also relatively less reactive methyl and benzyl esters could be used as a substrate. The reaction could be performed without strictly dry and anaerobic conditions and the 6-chloro-2-pyridone catalyst could be recovered quantitatively after reaction. The method could be applied to dipeptide synthesis from methyl or benzyl esters of amino acids, where a high enantiomeric purity of the products was maintained. The mechanism involving dual activation of ester and amine substrates through hydrogen bonding between catalyst and substrates is proposed where 6-halo-2-pyridones act as a bifunctional Br?nsted acid/base catalyst.

Graphical abstract: 6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis
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