Sulfonamides as novel terminators of cationic cyclisations.
Trifluoromethanesulfonic (triflic) acid is an excellent catalyst for inducing overall 5-endo cyclisation of homoallylic sulfonamides [e.g. 4] to give pyrrolidines [e.g. 5]. In competitive experiments, pyrrolidines or homopiperidines are formed in preference to piperidines, even when the latter would be obtained by trapping a tertiary carbocation. Cationic cascades terminated by a sulfonamide group are viable for the efficient formation of polycyclic systems.
Haskins
Charlotte M
CM
Chemistry Department, Cardiff University, P.O. Box 912, Cardiff, UK CF10 3TB.
Knight
David W
DW