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: Contribution to journalArticle

17 引用 (Scopus)

抜粋

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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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