Login / Signup

Esters as Alkynyl Acyl Ammonium and Azolium Precursors: A Formal [2 + 3] Annulation with Amidomalonates via Lewis Base/Lewis Acid Cooperative Catalysis.

Jing CaoKewen SunShuding DongTao LuYing DongDing Du
Published in: Organic letters (2017)
Esters are for the first time used as α,β-unsaturated alkynyl acyl ammonium and azolium precursors to undergo a formal [2 + 3] annulation with amidomalonates through DMAP/LiCl or carbene/LiCl cooperative catalysis. A wide range of (Z)-5-amino-3-furanones were obtained in moderate to high yields with high regioselectivity and stereoselectivity. In addition, a plausible mechanism based on the calculated charge distribution of the intermediates is proposed to explain the regioselectivity.
Keyphrases
  • ionic liquid
  • fatty acid
  • high intensity