Login / Signup

Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions.

Qinglin ZhangJiayin ZhangWangjie ZhuRuimin LuChang Guo
Published in: Nature communications (2024)
Precision control of stereochemistry in radical reactions remains a formidable challenge due to the prevalence of incidental racemic background reactions resulting from undirected substrate oxidation in the absence of chiral induction. In this study, we devised an thoughtful approach-electricity-driven asymmetric Lewis acid catalysis-to circumvent this impediment. This methodology facilitates both asymmetric dienylation and allylation reactions, resulting in the formation of all-carbon quaternary stereocenters and demonstrating significant potential in the modular synthesis of functional and chiral benzoxazole-oxazoline (Boox) ligands. Notably, the involvement of chiral Lewis acids in both the electrochemical activation and stereoselectivity-defining radical stages offers innovative departures for designing single electron transfer-based reactions, significantly underscoring the relevance of this approach as a multifaceted and universally applicable strategy for various fields of study, including electrosynthesis, organic chemistry, and drug discovery.
Keyphrases
  • drug discovery
  • electron transfer
  • ionic liquid
  • capillary electrophoresis
  • risk factors
  • room temperature
  • mass spectrometry
  • risk assessment
  • hydrogen peroxide
  • climate change