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 |
| 巻 | 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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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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TY - JOUR
T1 - Asymmetric Synthesis of Axially Chiral Benzocarbazole Derivatives Based on Catalytic Enantioselective Hydroarylation of Alkynes
AU - Arae, Sachie
AU - Beppu, Shota
AU - Kawatsu, Takahiro
AU - Igawa, Kazunobu
AU - Tomooka, Katsuhiko
AU - Irie, Ryo
PY - 2018/8/17
Y1 - 2018/8/17
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85051694384&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85051694384&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.8b01945
DO - 10.1021/acs.orglett.8b01945
M3 - Article
AN - SCOPUS:85051694384
VL - 20
SP - 4796
EP - 4800
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 16
ER -