DOI: 10.1002/ajoc.70520 ISSN: 2193-5807
Synthesis of Tetrasubstituted 2‐Pyrrolines via Zn(II)‐Catalyzed [3+2] Annulation of NH 2 ‐Enaminones and N‐Tosylaziridines
Qingna Yang, Yan Xie, Liang Xie, Xinying Li, Ziyan Wu, Yucai Jiang, Huiyan Lou, Lulu Chen, Changyuan ZhangABSTRACT
A Zn(II)‐catalyzed [3+2] annulation of NH 2 ‐enaminones with N‐tosylaziridines is described. Various NH 2 ‐enaminones, along with diversely substituted N‐tosylaziridines, underwent this transformation to deliver tetrasubstituted 2‐pyrrolines in 44%–98% yields under mild conditions. This protocol offers broad substrate scope, good functional group tolerance, and high regioselectivity. Additionally, the resulting tetrasubstituted 2‐pyrrolines could be oxidized to pyrrole (under air/TFA) or undergo tosyl migration (under KOH), highlighting their synthetic versatility.