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. Brambilla
Secondo
;
G. Abbiati
Penultimo
;
V. Pirovano
Ultimo
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.
Aza-Diels Alder; Imines; Nitrogen heterocycles; Spiroindolenine; Synthetic methods;
Settore CHIM/06 - Chimica Organica
apr-2021
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/839771
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