Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis
| Autor: | Yugen Zhu, Wei Wang, Chloe E. Pitsch, Wei He, Xiaotai Wang, Xiang Wang |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Indoles
Silver Alkyne Stereoisomerism 010402 general chemistry 01 natural sciences Article Catalysis chemistry.chemical_compound Nucleophile Organic chemistry Phosphoric Acids Phosphoric acid Indole test chemistry.chemical_classification Molecular Structure 010405 organic chemistry Hydrogen bond Enantioselective synthesis Hydrogen Bonding General Medicine General Chemistry 0104 chemical sciences chemistry Cyclization Alkynes |
| Zdroj: | Angewandte Chemie International Edition. 56:12206-12209 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201706694 |
| Popis: | We report the enantioselective synthesis of tetracyclic indolines using cooperative silver(I) and chiral phosphoric acid catalysis. A variety of alkyne-tethered indoles are suitable for this process. Mechanistic studies suggest that the in situ-generated silver(I) chiral phosphate activates both the alkyne and the indole nucleophile in the initial cyclization step through an intermolecular hydrogen bond and the phosphate anion promotes proton transfer. In addition, further modifications of the cyclization products enabled stereochemistry-function studies of a series of bioactive indolines. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text