DOI: 10.1002/asia.202300626 ISSN:

Stereoselective Synthesis of Pyrrolo/Pyrido[2,1‐a]isoindoles via Alkyne Iminium Ion Cyclization of Vinylogous Carbamates

Santosh J. Gharpure, Sanyog Kumari, Mahadev S. Sherikar
  • General Chemistry
  • Biochemistry
  • Organic Chemistry

An efficient, acid‐mediated, intramolecular alkyne iminium ion cyclization of oxoisoindolidene for the diastereoselective synthesis of pyrrolo/pyridoisoindole is described. This protocol features broad substrate scope and easy scalability. An unusual N to C‐1,3‐alkyl shift is observed with substrates bearing strong electron donating group at the phenyl ring attached to alkyne with concomitant hydration of alkyne to the ketone.

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