Indium(III)‐catalyzed Aza‐Conia‐Ene Reaction for the Synthesis of Indolizines

A new indium(III)‐catalyzed reaction for the synthesis of a series of indolizine scaffolds has been developed. This methodology was highly efficient, allowing a low catalyst loading of 2 mol % (down to 0.5 mol %) and rendering the products in high yields through a 5‐exo‐dig aza‐Conia‐ene reaction. F...

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Veröffentlicht in:Chemistry : a European journal 2017-06, Vol.23 (33), p.7905-7909
Hauptverfasser: Meazza, Marta, Leth, Lars A., Erickson, Jeremy D., Jørgensen, Karl Anker
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Sprache:eng
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Zusammenfassung:A new indium(III)‐catalyzed reaction for the synthesis of a series of indolizine scaffolds has been developed. This methodology was highly efficient, allowing a low catalyst loading of 2 mol % (down to 0.5 mol %) and rendering the products in high yields through a 5‐exo‐dig aza‐Conia‐ene reaction. Furthermore, the possibility of incorporating an electrophile into the generated pyrrolidone ring in a one‐pot synergistic fashion was demonstrated. Finally, based on experimental observations, a mechanism proposal was outlined. Building heterocyclic scaffolds: A new indium(III)‐catalyzed reaction for the synthesis of a series of indolizine scaffolds has been developed. This methodology is highly efficient, allowing a low catalyst loading of 2 mol % (down to 0.5 mol %) and rendering the products in high yields through a 5‐exo‐dig aza‐Conia‐ene reaction. Furthermore, the possibility of incorporating an electrophile into the generated pyrrole ring in a one‐pot synergistic fashion is demonstrated. Finally, based on experimental observations, a mechanism proposal is outlined.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201701820