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Enantioselective N-Heterocyclic Carbene Catalyzed Cyclopentene Synthesis via the β-Azolium Ylide.

Lydia ScottYuji NakanoChanghe ZhangDavid W Lupton
Published in: Angewandte Chemie (International ed. in English) (2018)
Herein we report the cycloisomerization of electron-poor 1,5-dienes via the β-azolium ylide to give enantioenriched cyclopentenes. The reaction is mediated by a chiral N-heterocyclic carbene (NHC) catalyst, exploits readily available substrates, has good generality (17 examples), and displays excellent enantioselectivity (mostly >94:6). Studies demonstrating the viability of a related dynamic kinetic resolution are reported, as are those with alternate tethers and derivatizations.
Keyphrases
  • room temperature
  • ionic liquid
  • highly efficient
  • electron transfer
  • single molecule
  • case control
  • capillary electrophoresis
  • carbon dioxide