Login / Signup

Enantioselective N-Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium.

Rachel M GillardJared E M FernandoDavid W Lupton
Published in: Angewandte Chemie (International ed. in English) (2018)
Herein we report the enantioselective N-heterocyclic carbene catalyzed (4+2) annulation of the dienyl acyl azolium with enolates. The reaction exploits readily accessible acyl fluorides and TMS enol ethers to give a range of highly enantio- and diastereo-enriched cyclohexenes (most >97:3 er and >20:1 dr). The reaction was found to require high nucleophilicity NHC catalysts with mechanistic studies supporting a stepwise 1,6-addition/β-lactonization.
Keyphrases
  • fatty acid
  • room temperature
  • highly efficient
  • estrogen receptor
  • case control
  • metal organic framework