Sulfonamides as novel terminators of cationic cyclisations |
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Authors: | Haskins Charlotte M Knight David W |
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Affiliation: | Chemistry Department, Cardiff University, P.O. Box 912, Cardiff, UK CF10 3TB. |
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Abstract: | 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. |
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