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Cesium Carbonate Promoted Direct Amidation of Unactivated Esters with Amino Alcohol Derivatives.
Kuo, Chih-Hung; Hsieh, Wen-Tsai; Yang, Ya-Hsu; Hwang, Teng-Li; Cheng, Yu-Shan; Lin, Yuya A.
Afiliação
  • Kuo CH; Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
  • Hsieh WT; Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
  • Yang YH; Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
  • Hwang TL; Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
  • Cheng YS; Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
  • Lin YA; Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
J Org Chem ; 89(7): 4958-4970, 2024 Apr 05.
Article em En | MEDLINE | ID: mdl-38523317
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.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Taiwan

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Taiwan