Asymmetric Synthesis of Axially Chiral Benzocarbazole Derivatives Based on Catalytic Enantioselective Hydroarylation of Alkynes
| Autor: | Sachie Arae, Kazunobu Igawa, Katsuhiko Tomooka, Ryo Irie, Shota Beppu, Takahiro Kawatsu |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Indole test 010405 organic chemistry Organic Chemistry Enantioselective synthesis Alkyne Cinchonine 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Stereospecificity chemistry Intramolecular force Moiety Physical and Theoretical Chemistry Cinchonidine |
| Zdroj: | Organic letters. 20(16) |
| ISSN: | 1523-7052 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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