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]
Titolo: | Formal Aza‐Diels‐Alder Reactions of Spiroindolenines with Electronrich Dienes | |
Autori: | BRAMBILLA, ELISA (Secondo) ABBIATI, GIORGIO (Penultimo) PIROVANO, VALENTINA (Ultimo) | |
Parole Chiave: | Aza-Diels Alder; Imines; Nitrogen heterocycles; Spiroindolenine; Synthetic methods; | |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica | |
Data di pubblicazione: | 7-mag-2021 | |
Rivista: | ||
Tipologia: | Article (author) | |
Data ahead of print / Data di stampa: | apr-2021 | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/ejoc.202100251 | |
Appare nelle tipologie: | 01 - Articolo su periodico |
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