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Synthesis of 3‑(Arylsulfonyl)-3-pyrrolines from Allenyl Sulfonamides by Silver Ion Catalysis

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journal contribution
posted on 31.08.2018, 20:19 by Rama Rao Tata, Chencheng Fu, Steven P. Kelley, Michael Harmata
Treatment of allenyl sulfonamides with catalytic amounts of silver fluoride in acetonitrile at reflux afforded the corresponding 3-sulfonyl-3-pyrrolines in excellent yields by intramolecular hydroamination via a 5-endo-trig cyclization. The starting allenyl sulfonamides were prepared by lithiation of allenic sulfones and trapping with various N-sulfonylimines.