499782-23-9Relevant academic research and scientific papers
General and scalable amide bond formation with epimerization-prone substrates using T3P and pyridine
Dunetz, Joshua R.,Xiang, Yanqiao,Baldwin, Aaron,Ringling, Justin
supporting information; experimental part, p. 5048 - 5051 (2011/11/29)
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.
Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides
Escorihuela, Jorge,Burguete, M. Isabel,Luis, Santiago V.
scheme or table, p. 6885 - 6888 (2009/04/07)
A series of α-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)2 catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process.
