In the last decades intramolecular gold-catalyzed transformations have been broadly studied giving access to a series of relevant scaffolds. Among unsaturated substrates allenes offered a complete versatility participating in [2+2], [4+2] and [4+3] cyclizations. In contrast, the development of an intermolecular version of these transformations remains less explored. In this context significant [2+2] and [4+2] cycloadditions have been recently reported,1 including examples of enantioselective versions. Due to our interest in the preparation of functionalized carbazoles derivatives4 and considering the recent employment of N-allenamides in intermolecular cycloaddition reactions,1,2 we decided to study the viability of gold-catalyzed cycloaddition between allenes and vinyl indoles, which might offer a simple and selective access to these relevant structures. Thus, it was found that an appropriate choice of the substituent at N-1 of the indole and of reaction conditions enabled the selective preparation of isomeric tetrahydrocarbazoles 3, 3’ and of unexpected compound 4, arose from an unusual multicomponent cascade sequence. With optimized reaction conditions in hand, it was possible to evaluate the scope of these transformations varying both the vinyl indole and the N-allenamide moieties. A mechanism for the formation of the products through a formal [4+2] cycloaddition reaction has been proposed and supported by experimental evidences.

Gold catalyzed synthesis of tetrahydrocarbazole derivatives through an intermolecular cycloaddition of vinyl indoles and N-allenamides / V. Pirovano, L. Decataldo, R. Vicente, E. Rossi. ((Intervento presentato al convegno Frontiers in Chemistry Armenia tenutosi a Yerevan nel 2013.

Gold catalyzed synthesis of tetrahydrocarbazole derivatives through an intermolecular cycloaddition of vinyl indoles and N-allenamides

V. Pirovano
Primo
;
E. Rossi
Ultimo
2013-08-29

Abstract

In the last decades intramolecular gold-catalyzed transformations have been broadly studied giving access to a series of relevant scaffolds. Among unsaturated substrates allenes offered a complete versatility participating in [2+2], [4+2] and [4+3] cyclizations. In contrast, the development of an intermolecular version of these transformations remains less explored. In this context significant [2+2] and [4+2] cycloadditions have been recently reported,1 including examples of enantioselective versions. Due to our interest in the preparation of functionalized carbazoles derivatives4 and considering the recent employment of N-allenamides in intermolecular cycloaddition reactions,1,2 we decided to study the viability of gold-catalyzed cycloaddition between allenes and vinyl indoles, which might offer a simple and selective access to these relevant structures. Thus, it was found that an appropriate choice of the substituent at N-1 of the indole and of reaction conditions enabled the selective preparation of isomeric tetrahydrocarbazoles 3, 3’ and of unexpected compound 4, arose from an unusual multicomponent cascade sequence. With optimized reaction conditions in hand, it was possible to evaluate the scope of these transformations varying both the vinyl indole and the N-allenamide moieties. A mechanism for the formation of the products through a formal [4+2] cycloaddition reaction has been proposed and supported by experimental evidences.
gold catalysis; homogeneous catalysis; indole, cycloaddition; heterocyclic
Settore CHIM/06 - Chimica Organica
Gold catalyzed synthesis of tetrahydrocarbazole derivatives through an intermolecular cycloaddition of vinyl indoles and N-allenamides / V. Pirovano, L. Decataldo, R. Vicente, E. Rossi. ((Intervento presentato al convegno Frontiers in Chemistry Armenia tenutosi a Yerevan nel 2013.
Conference Object
File in questo prodotto:
File Dimensione Formato  
ACF2013_C24_Pirovano.pdf

accesso aperto

Descrizione: Abstract
Tipologia: Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione 140.39 kB
Formato Adobe PDF
140.39 kB Adobe PDF Visualizza/Apri
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: http://hdl.handle.net/2434/608960
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact