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

研究成果: ジャーナルへの寄稿記事

10 引用 (Scopus)

抄録

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.

元の言語英語
ページ(範囲)4796-4800
ページ数5
ジャーナルOrganic Letters
20
発行部数16
DOI
出版物ステータス出版済み - 8 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

これを引用

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.

:: Organic Letters, 巻 20, 番号 16, 17.08.2018, p. 4796-4800.

研究成果: ジャーナルへの寄稿記事

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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.",
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AU - Irie, Ryo

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