AG-041R is a chiral, enantiopure 2-oxindole urea derivative provided with a remarkable bio-activity that ranges from anti-ulcer, to condrogenic and anti-proliferative. Following the introduction by our group of a convenient protocol for the organocatalytic, asymmetric alpha-amination (AaA) of N-unprotected 3-alkyl-2-oxindoles with bis(trichloroethyl)¬azodicarboxylate (BTCEAD), we report herein a novel route to AG-041R, which takes advantage of the prompt elaboration of chiral hydrazine derivatives masked as trichloroethyl carbamates. In addition to the optimization of the AA step and the subsequent elaboration of the resulting aminated product, the possibility to enhance the enantiomeric purity of suitable intermediates, by selective crystallization of the racemate, will be briefly discussed.

Catalytic enantioselective alpha-amination of 2-oxindoles and a new route to the bio-active compound AG-041R

Stefano Bonciolini
Membro del Collaboration Group
;
Mattia Bondanza
Membro del Collaboration Group
;
Alessandro Mandoli
Supervision
2023-01-01

Abstract

AG-041R is a chiral, enantiopure 2-oxindole urea derivative provided with a remarkable bio-activity that ranges from anti-ulcer, to condrogenic and anti-proliferative. Following the introduction by our group of a convenient protocol for the organocatalytic, asymmetric alpha-amination (AaA) of N-unprotected 3-alkyl-2-oxindoles with bis(trichloroethyl)¬azodicarboxylate (BTCEAD), we report herein a novel route to AG-041R, which takes advantage of the prompt elaboration of chiral hydrazine derivatives masked as trichloroethyl carbamates. In addition to the optimization of the AA step and the subsequent elaboration of the resulting aminated product, the possibility to enhance the enantiomeric purity of suitable intermediates, by selective crystallization of the racemate, will be briefly discussed.
2023
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/1196248
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact