A study on the SN2-type ring opening reactions of aziridines with indoles as nucleophiles is reported. Under gold(I) catalysis a great variety of tryptamine derivatives were prepared in good to excellent yields with complete stereocontrol when chiral aziridines were used. We demonstrated that cationic gold(I) catalysts are superior Lewis acids to the previously reported group 3, 12 and 13 metals in term of catalyst loading and reaction yields. Moreover, complete regioselectivity was observed for 2-phenyl-N-tosylaziridine; whereas, regioselectivity up to 10:1 ratio was observed with 2-methyl-N-tosylaziridine. Finally, a preliminary study on the dearomatization reactions giving rise to pyrroloindolines is also reported.

Exploiting the σ-phylic properties of cationic gold(I) catalysts in the ring opening reactions of aziridines with indoles / E. Rossi, G. Abbiati, M. Dell’Acqua, M. Negrato, A. Paganoni, V. Pirovano. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 14(2016), pp. 6095-6110.

Exploiting the σ-phylic properties of cationic gold(I) catalysts in the ring opening reactions of aziridines with indoles

E. Rossi
Primo
;
G. Abbiati
Secondo
;
M. Dell’Acqua;V. Pirovano
Ultimo
2016

Abstract

A study on the SN2-type ring opening reactions of aziridines with indoles as nucleophiles is reported. Under gold(I) catalysis a great variety of tryptamine derivatives were prepared in good to excellent yields with complete stereocontrol when chiral aziridines were used. We demonstrated that cationic gold(I) catalysts are superior Lewis acids to the previously reported group 3, 12 and 13 metals in term of catalyst loading and reaction yields. Moreover, complete regioselectivity was observed for 2-phenyl-N-tosylaziridine; whereas, regioselectivity up to 10:1 ratio was observed with 2-methyl-N-tosylaziridine. Finally, a preliminary study on the dearomatization reactions giving rise to pyrroloindolines is also reported.
Gold; Aziridines; Indoles; Tryptamines; Pyrroloindolines
Settore CHIM/06 - Chimica Organica
2016
Article (author)
File in questo prodotto:
File Dimensione Formato  
accepted manuscript.pdf

embargo fino al 01/07/2017

Descrizione: Accepted Manuscript
Tipologia: Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione 748.08 kB
Formato Adobe PDF
748.08 kB Adobe PDF Visualizza/Apri
c6ob00672h.pdf

accesso riservato

Tipologia: Publisher's version/PDF
Dimensione 1.12 MB
Formato Adobe PDF
1.12 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

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/2434/388600
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 24
  • ???jsp.display-item.citation.isi??? 22
social impact