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Stereospecific [3+2] Cycloaddition of Chiral Arylallenes with C,N-Cyclic Azomethine Imines.

De WangXinyu LiuManjaly J AjithaZhixin LiuYongyi HuKuo-Wei Huang
Published in: Organic letters (2023)
A novel α,β-regioselective [3+2] cycloaddition reaction of arylallene with C,N-cyclic azomethine imine is reported. The axial-to-central chirality transfer phenomenon has been disclosed with chiral allenes in the reaction. The wide substrate scope, including different functional groups and natural products, reveals the generality of the methodology. Both experiments and density functional theory calculations have been used to elucidate a plausible mechanism.
Keyphrases
  • density functional theory
  • molecular dynamics
  • capillary electrophoresis
  • electron transfer
  • ionic liquid
  • amino acid