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

10 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

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Alkynes
indoles
alkynes
Derivatives
Reaction intermediates
reaction intermediates
Cyclization
quinones
vinylidene
synthesis
Catalysis
catalysis
Transition metals
Metals
transition metals
catalysts
Catalysts
indole
quinone methide
cinchonine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Asymmetric Synthesis of Axially Chiral Benzocarbazole Derivatives Based on Catalytic Enantioselective Hydroarylation of Alkynes. / Arae, Sachie; Beppu, Shota; Kawatsu, Takahiro; Igawa, Kazunobu; Tomooka, Katsuhiko; Irie, Ryo.

In: Organic Letters, Vol. 20, No. 16, 17.08.2018, p. 4796-4800.

Research output: Contribution to journalArticle

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