General and Scalable Amide Bond Formation with Epimerization-Prone Substrates Using T3P and Pyridine

Autor:	Joshua R. Dunetz, Justin Ringling, Yanqiao Xiang, Aaron F. Baldwin
Rok vydání:	2011
Předmět:	Molecular Structure Pyridines Chemistry Organic Chemistry Organophosphonates Stereoisomerism Amides Biochemistry Catalysis Acid anhydride Propane chemistry.chemical_compound Pyridine Glucokinase activator Peptide bond Organic chemistry Molecule Epimer Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 13:5048-5051
ISSN:	1523-7052 1523-7060
Popis:	The mild combination of T3P (n-propanephosphonic acid anhydride) and pyridine has been developed for low-epimerization amide bond formation and implemented for the synthesis of a key intermediate to a glucokinase activator. This robust method is general for the coupling of various racemization-prone acid substrates and amines, including relatively non-nucleophilic anilines, and provides amides in high yields with very low epimerization. With easy reaction setup and product isolation, this protocol offers several practical and experimental benefits.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e6d3ea227f54c97bd604da78a9e64a6d https://doi.org/10.1021/ol201875q Zobrazit plný text záznamu