3 years ago

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

Indium(III)-catalyzed Aza-Conia-Ene Reaction for the Synthesis of Indolizines
Karl Anker Jørgensen, Marta Meazza, Lars A. Leth, Jeremy D. Erickson
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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701820

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