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Indium(III)‐catalyzed Aza‐Conia‐Ene Reaction for the Synthesis of Indolizines
Author(s) -
Meazza Marta,
Leth Lars A.,
Erickson Jeremy D.,
Jørgensen Karl Anker
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701820
Subject(s) - indolizine , indium , catalysis , electrophile , ene reaction , chemistry , rendering (computer graphics) , combinatorial chemistry , reaction mechanism , medicinal chemistry , organic chemistry , computer science , computer graphics (images)
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.