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

• DOI: 10.1021/acs.orglett.8b02440
• Publication Date: 2018-09-04T12:01:21Z
• Authors: Rama Rao Tata; Chencheng Fu; Steven P. Kelley; Michael Harmata
• Keywords: 01 natural sciences; 0104 chemical sciences

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.