The phosphate-carboxylate mixed-anhydride method: a mild, efficient process for ester and amide bond construction

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• 作者：James McNulty^a ; ^{jmcnult@mcmaster.ca} ; Ramesh Vemula^a ; Venkatesan Krishnamoorthy^a ; Al Robertson^b
• 关键词：Acylation ; Mixed-anhydride ; Ester ; Amide ; Chiral amines ; Organocatalysis
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：8 July, 2012
• 卷：68
• 期：27-28
• 页码：5415-5421
• 文件大小：1719 K

摘要

A highly efficient carboxylate-phosphate anhydride pathway is described for the direct, economical synthesis of esters and amides from carboxylic acids and alcohols or amines. The reaction proceeds with retention of configuration with both chiral secondary alcohols and 伪-amino acid derivatives allowing access to useful chiral auxiliaries, ligands, and organocatalysts. Ester and amide products can be isolated directly in high yield due to the water soluble nature of the side products.