Spiroindolenines were employed as cyclic imine substrates in formal aza-Diels-Alder reactions with Danishefsky’s diene or silyloxy-substituted electron-rich dienes for the synthesis of the corresponding tetrahydropyrido[1,2-a]spiroindolinones. The reactions occur under mild conditions in the presence of ytterbium triflate as Lewis acidic catalyst delivering the desired compounds in good yield. The reaction results in the preparation of a small library of a new class of conformational constrained heterocyclic derivatives that easily undergo selective and efficient manipulations.
Formal Aza‐Diels‐Alder Reactions of Spiroindolenines with Electronrich Dienes / E. Rossi, E. Brambilla, S. Leoni, G. Abbiati, V. Pirovano. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2021:17(2021 May 07), pp. 2440-2447. [10.1002/ejoc.202100251]
Formal Aza‐Diels‐Alder Reactions of Spiroindolenines with Electronrich Dienes
E. Rossi
Primo
;E. BrambillaSecondo
;G. AbbiatiPenultimo
;V. PirovanoUltimo
2021
Abstract
Spiroindolenines were employed as cyclic imine substrates in formal aza-Diels-Alder reactions with Danishefsky’s diene or silyloxy-substituted electron-rich dienes for the synthesis of the corresponding tetrahydropyrido[1,2-a]spiroindolinones. The reactions occur under mild conditions in the presence of ytterbium triflate as Lewis acidic catalyst delivering the desired compounds in good yield. The reaction results in the preparation of a small library of a new class of conformational constrained heterocyclic derivatives that easily undergo selective and efficient manipulations.File | Dimensione | Formato | |
---|---|---|---|
accepted articleejoc.202100251.pdf
Open Access dal 02/04/2022
Descrizione: post-print
Tipologia:
Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione
1.37 MB
Formato
Adobe PDF
|
1.37 MB | Adobe PDF | Visualizza/Apri |
ejoc.202100251(1).pdf
accesso riservato
Tipologia:
Publisher's version/PDF
Dimensione
5.07 MB
Formato
Adobe PDF
|
5.07 MB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.