Sulfur-directed 5-exo selective aryl radical cyclization onto enamide: A simple route to chilenine

Article abstract of DOI:10.1016/00404-0399(50)1364-N

Bu₃SnH-mediated aryl radical cyclization of the N-(o-bromoaroyl)enamine 5 took place in a 5-exo-trig manner exclusively to give isoindolone 7, which was transformed into the key intermediate 11 for the synthesis of isoindolobenzazepine alkaloid chilenine (2).