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Catalytic Atroposelective Synthesis of N-N Axially Chiral Indolylamides.

Tian-Zhen LiShu-Fang WuNing-Yi WangChen-Shengping HongYu-Chen ZhangFeng Shi
Published in: The Journal of organic chemistry (2024)
The catalytic atroposelective synthesis of N-N axially chiral indolylamides was established via dynamic kinetic resolution, which makes use of chiral Lewis base-catalyzed asymmetric acylation of N -acylaminoindoles as a new type of platform molecule with anhydrides. By this strategy, a series of N-N axially chiral indolylamides were synthesized in overall good yields (up to 98%) with excellent enantioselectivities (up to 99% ee). Moreover, some of these N-N axially chiral indolylamides display some extent of anticancer activity, which demonstrates their potential application in medicinal chemistry. Therefore, this work has not only provided a new strategy for the synthesis of N-N axially chiral monoaryl indoles but also offered a new member of N-N axially chiral monoaryl indoles with configurational stability and promising application, thereby solving the challenges in atroposelective synthesis and application of N-N axially chiral monoaryl indoles.
Keyphrases
  • capillary electrophoresis
  • ionic liquid