Asymmetric Synthesis of Axially Chiral Benzocarbazole Derivatives Based on Catalytic Enantioselective Hydroarylation of Alkynes

Sachie Arae, Shota Beppu, Takahiro Kawatsu, Kazunobu Igawa, Katsuhiko Tomooka, Ryo Irie

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A new synthetic approach to novel axially chiral benzocarbazole derivatives based on the highly enantioselective intramolecular hydroarylation (94-96% ee) of linked alkyne-indole systems by using the prevalent chiral base catalyst, cinchonidine or cinchonine, under unprecedented transition-metal-free conditions is described. The process is considered to involve chiral base catalysis for enantioselective transformation of the alkyne part to a reaction intermediate with an axially chiral vinylidene o-quinone methide (VQM) functionality, which subsequently effects stereospecific cyclization with the tethered indole moiety.

Original languageEnglish
Pages (from-to)4796-4800
Number of pages5
JournalOrganic Letters
Volume20
Issue number16
DOIs
Publication statusPublished - Aug 17 2018

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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