Synfacts 2019; 15(10): 1185
DOI: 10.1055/s-0039-1690907
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

The Steglich Esterification

Benjamin List
Benjamin Mitschke
Neises B, Steglich W. * Friedrich-Wilhelms-Universität Bonn, Germany
Simple Method for the Esterification of Carboxylic Acids.

Angew. Chem., Int. Ed. Engl. 1978;
17: 522-524
Further Information

Publication History

Publication Date:
17 September 2019 (online)



In 1978, Neises and Steglich showed that a catalytic amount of DMAP can drastically enhance reactivity in carbodiimide-activated esterification reactions. This method not only improved the yields of the products while shortening the reaction times, but also permitted the construction of, at that date, inaccessible molecules. In later years, this protocol has become one of the most frequently used esterification strategies, with a tremendous impact on both academia and industry.



In carbodiimide-mediated carboxylic acid activation reactions, the corresponding O-acyl­urea is the most relevant intermediate. When poor nucleophiles are used, side reactions prevail and lead to diminished yields or complete lack of productive reactivity. DMAP (previously introduced by Litvinenko and Kirichenko, see: Dok. Akad. Nauk SSSR, Ser. Khim. 1967, 176, 97) directly accepts the acyl group from the O-acylurea, thereby preventing possible side reactions and effectively transferring it to the respective nucleophile.