Phosphazene base-catalyzed hydroamination of aminoalkenes for the construction of isoindoline scaffolds: Application to the total synthesis of aristocularine
2022
Matsuoka, Junpei | Terashita, Maki | Miyawaki, Akari | Tomioka, Kiyoshi | Yamamoto, Yasutomo
A method for isoindoline synthesis via phosphazene base-catalyzed intramolecular hydroamination of aminoalkenes was developed. The reaction has a broad functional group tolerance, including for halide, cyano, and methoxy groups, and could also be used to synthesize tetrahydroisoquinoline, pyrrolidine, and piperidine. The method was used as a key step in the total synthesis of aristocularine in six steps in 35% overall yield. The strategy involved the construction of an isoindoline core through controlling the formation of the desired CN bond, with the relatively labile methoxymethyl group and arylbromide remaining intact.
Afficher plus [+] Moins [-]Mots clés AGROVOC
Informations bibliographiques
Cette notice bibliographique a été fournie par National Agricultural Library
Découvrez la collection de ce fournisseur de données dans AGRIS