Application of Isocyanides Derived from α-Amino Acids as Substrates for the Ugi Reaction

Autor:	Stanislaw Berlozecki, Ryszard Ostaszewski, Wiktor Szymanski
Rok vydání:	2008
Předmět:	Solvent chemistry.chemical_classification chemistry.chemical_compound Enantiopure drug Chemistry Organic Chemistry Ugi reaction Organic chemistry Lewis acids and bases Racemization Dichloromethane Lewis acid catalysis Amino acid
Zdroj:	Synthetic Communications. 38:2714-2721
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397910802222787
Popis:	A systematic study on the influence of Lewis acid, solvent, and temperature on the stereochemical course of the Ugi reaction was performed to find conditions in which the isocyanides derived from enantiopure α-amino acids do not racemize. After a series of experiments, dichloromethane was used as a solvent and BF3 · OEt2 as a Lewis acid catalyst. This combination allowed us to obtain a product in a model reaction with 99% diastereoisomeric ratio (dr), with the structure motif of a group of cathepsin K inhibitors.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f5b1ada32323f541c6c64340895b97ff https://doi.org/10.1080/00397910802222787 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.