Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 17, Pages 2440-2447Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100251
Keywords
Aza-Diels-Alder; Imines; Nitrogen heterocycles; Spiroindolenine; Synthetic methods
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Spiroindolenines were used as cyclic imine substrates in formal aza-Diels-Alder reactions with Danishefsky's diene or silyloxy-substituted electron-rich dienes, leading to the synthesis of tetrahydropyrido[1,2-a]spiroindolinones under mild conditions in the presence of ytterbium triflate as a Lewis acidic catalyst, with good yields. 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.
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.
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