Synthesis of Dipeptide, Amide, and Ester without Racemization by Oxalyl Chloride and Catalytic Triphenylphosphine Oxide

Autor:	Meng-Nan Tong, Yufen Zhao, Ji-Wei Ren, Feng Ni
Rok vydání:	2021
Předmět:	Organic Chemistry Reactive intermediate Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Nucleophile Oxalyl chloride Amide Carboxylate Physical and Theoretical Chemistry Triphenylphosphine Racemization Triphenylphosphine oxide
Zdroj:	Organic Letters. 23:7497-7502
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c02614
Popis:	An efficient triphenylphosphine oxide-catalyzed amidation and esterification for the rapid synthesis of a series of dipeptides, amides, and esters is described. This reaction is applicable to challenging couplings of hindered carboxylic acids with weakly nucleophilic amines or alcohols, giving the products in good yields (67-90%) without racemization. This system employs the highly reactive intermediate Ph3PCl2 as the activator of the carboxylate in a catalytic manner and drives the reaction to completion in a short reaction time (less than 10 min).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b28d0f1effcab00dea3ce225e387062f https://doi.org/10.1021/acs.orglett.1c02614 Zobrazit plný text záznamu