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A Strategy for Synthesizing Axially Chiral Naphthyl-Indoles: Catalytic Asymmetric Addition Reactions of Racemic Substrates.

Fei JiangKe-Wei ChenPing WuYu-Chen ZhangYinchun JiaoFeng Shi
Published in: Angewandte Chemie (International ed. in English) (2019)
A new strategy for enantioselective synthesis of axially chiral naphthyl-indoles has been established through catalytic asymmetric addition reactions of racemic naphthyl-indoles with bulky electrophiles. Under chiral phosphoric acid catalysis, azodicarboxylates and o-hydroxybenzyl alcohols served as bulky but reactive electrophiles that were attacked by C2-unsubstituted naphthyl-indoles, which underwent a dynamic kinetic resolution to afford two series of axially chiral naphthyl-indoles in good yields (up to 98 %) and high enantioselectivities (up to 98:2 er).
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • crystal structure
  • single molecule
  • visible light