Base-promoted direct amidation of esters: beyond the current scope and practical applications |
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| Authors: | Ivaylo Slavchev Jas. S. Ward Kari Rissanen Georgi M. Dobrikov Svilen Simeonov |
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| Affiliation: | Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 9, Sofia 1113 Bulgaria.; University of Jyvaskyla, Department of Chemistry, Survontie 9 B, 40014 Jyväskylä Finland ; Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon Portugal |
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| Abstract: | The base-promoted direct amidation of unactivated esters is among the most useful reactions for amide bond formation in contemporary organic chemistry. The intensive research in this area has led to the development of a number of new methods to achive this transformation. However, to date, the existing literature is more methodological and in many instances lacks practical directions. Therefore, the full potential of this transformation is yet to be revealed by broadening the substrate scope. In a search for new practical applications of the amidation reaction, herein we present a comprehensive study of a number of base-promoted direct amidations that encompass a wide range of amines and esters. Furthermore, we applied our findings in the synthesis of phosphoramidates and several industrially relevant products.A new method for direct amidation of unactivated esters with unprecedented substrate scope is developed. |
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