Cesium Carbonate Promoted Direct Amidation of Unactivated Esters with Amino Alcohol Derivatives

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Mar 25

PMID 38523317

Authors

Chih-Hung Kuo

Wen-Tsai Hsieh

Ya-Hsu Yang

Teng-Li Hwang

Yu-Shan Cheng

Yuya A Lin

Affiliations

Soon will be listed here.

Abstract

Cesium carbonate promoted direct amidation of unactivated esters with amino alcohols was developed without the use of transition-metal catalysts and coupling reagents. This method enabled the synthesis of several serine-containing oligopeptides and benzamide derivatives with yields up to 90%. The methodology proceeds under mild reaction conditions and exhibits no racemization for most naturally occurring amino acid substrates. The reaction demonstrates good compatibility with primary alkyl and benzyl esters and broad tolerance for a range of amino acid substrates with nonpolar and protected side chains. The hydroxy group on the amine nucleophile was found to be critical for the reaction to be successful. A likely mechanism involving cesium coordination to the substrates enabling the subsequent proximity-driven acyl transfer was proposed. The practicality of this approach was demonstrated in the preparation of a biologically active nicotinamide derivative in a reasonable yield.

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