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Kinetic Resolution of Helicenols via Palladium-Catalyzed Atroposelective C-C Bond Cleavage/Ring-Opening Reaction.

Zhen ChenHan YangLin LiLonghui DuanJunwei XiZhenhua Gu
Published in: Organic letters (2024)
Helicenes represent a class of inherently chiral structures that lack conventional chiral elements, such as stereogenic centers, chiral axes, or plane. The asymmetric synthesis of these helical compounds can be particularly challenging as a result of their pronounced molecular strain. In this study, we report a palladium-catalyzed atroposelective carbon-carbon bond cleavage reaction of helical tertiary alcohols. Because the helical alcohols are configurationally stable, the reaction proceeded through a kinetic resolution pathway, resulting in achieving optically active helicenols alongside the sterically hindered axially chiral products.
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • single molecule
  • electron transfer
  • dna binding
  • high resolution