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Anion-accelerated asymmetric Nazarov cyclization: access to vicinal all-carbon quaternary stereocenters.

Cody F DickinsonGlenn P A YapMarcus A Tius
Published in: Organic & biomolecular chemistry (2023)
We have developed a catalytic asymmetric Nazarov cyclization that results in the formation of two contiguous all-carbon quaternary stereocenters in high yield with excellent levels of asymmetric induction. This method requires no catalyst recognition elements in the starting materials that are simple diketoesters. Geometrically pure E or Z isomers of the starting material lead to diastereomerically pure products with high enantioselectivity because the species that undergoes cyclization is a rhodium enolate that is configurationally stable.
Keyphrases
  • ionic liquid
  • solid state
  • room temperature
  • reduced graphene oxide