Stereoselective Synthesis of Pyrrolo/Pyrido[2,1‐a]isoindoles via Alkyne Iminium Ion Cyclization of Vinylogous CarbamatesSantosh J. Gharpure, Sanyog Kumari, Mahadev S. Sherikar
- General Chemistry
- 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.