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Catalyst-Controlled Product Selectivity for Cycloaddition of Bis(indol-3-yl)-allenes to Fused Spiroindolines and Mechanistic Studies.

Yan-Yan ZhangYin WeiMin Shi
Published in: Organic letters (2019)
A catalyst-controlled cycloaddition reaction of bis(indol-3-yl)-allenes gives rise to two different types of fused spiroindolines bearing a spiro quaternary stereocenter, affording a range of fused spiroindolines in good yields. The asymmetric desymmetrization of bis(indol-3-yl)-allenes with very high regioselectivities and excellent enantioselectivities has been successfully established and catalyzed by (R)-DTBM-Segphos(AuNTf2)2. Mechanistic studies through control experiments and DFT calculations provide plausible mechanistic proposals.
Keyphrases
  • ionic liquid
  • room temperature
  • density functional theory
  • case control
  • highly efficient
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  • molecular dynamics
  • metal organic framework
  • carbon dioxide
  • molecular docking
  • solid state