A novel direct catalytic asymmetric synthesis of cyclic indole derivatives by intramolecular carbopalladation of allenes and subsequent intramolecular amination
| Autor: | Kunio Hiroi, Ikuko Abe, Yuko Hiratsuka, Fumiko Kato, Kazuhiro Watanabe, Mayumi Hiroi |
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| Rok vydání: | 2002 |
| Předmět: |
inorganic chemicals
Indole test Stereochemistry organic chemicals Organic Chemistry Enantioselective synthesis Substrate (chemistry) Combinatorial chemistry Catalysis Inorganic Chemistry Solvent chemistry.chemical_compound chemistry Intramolecular force heterocyclic compounds Physical and Theoretical Chemistry Phosphine Amination |
| Zdroj: | Tetrahedron: Asymmetry. 13:1351-1353 |
| ISSN: | 0957-4166 |
| Popis: | A novel asymmetric synthetic method allowing a facile entry to chiral cyclic indole compounds has been developed by means of asymmetric carbopalladation–amination of allenes using a palladium catalyst with chiral phosphine ligands: intramolecular carbopalladation of allenes, which bear o-iodophenyl amino groups, was followed by intramolecular amination of the resultant π-allylpalladium intermediates. The enantioselectivity of the asymmetric reactions were found to be dependant on the chiral phosphine ligands and the solvent used; N-methylpyridone was the most effective solvent for achieving efficient enantioselectivity with high chemical yields, and (S)-(−)-BINAP or (S)-Tol-BINAP were revealed to be the most useful of the chiral phosphine ligands examined, depending on the substrate employed. |
| Databáze: | OpenAIRE |
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