Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres
| Autor: | Line Næsborg, Karl Anker Jørgensen, Henriette N. Tobiesen, Thanh V. Q. Nguyen, Nomaan M. Rezayee, Vibeke Henriette Lauridsen |
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| Rok vydání: | 2019 |
| Předmět: |
Indole test
010405 organic chemistry Chemistry Enantioselective synthesis AMINES General Chemistry Oxidative phosphorylation ALKYLATION 010402 general chemistry 01 natural sciences ALPHA-ARYLATION 0104 chemical sciences Catalysis Yield (chemistry) Organic chemistry Stereoselectivity Quaternary carbon |
| Zdroj: | Chemical Science Rezayee, N, Lauridsen, V H, Naesborg, L, Nguyen, T V Q, Tobiesen, H N & Jorgensen, K A 2019, ' Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres ', Chemical Science, vol. 10, no. 12, pp. 3586-3591 . https://doi.org/10.1039/c9sc00196d |
| ISSN: | 2041-6520 |
| DOI: | 10.1039/c9sc00196d |
| Popis: | The first organocatalysed, metal-free cross-nucleophile coupling of indoles with α-branched aldehydes forming acyclic stereoselective quaternary carbon centres is presented. The first organocatalysed, metal-free cross-nucleophile coupling of indoles with α-branched aldehydes forming acyclic stereoselective quaternary carbon centres is presented. Applying an amino acid-derived catalyst with suitable organic oxidants affords the desired enantioenriched indole functionalised products with moderate to excellent yield and enantioselectivity. Two metal-free oxidative protocols employing either DDQ or a sequential approach that uses two organocatalysts to facilitate the use of O2 as the terminal oxidant are disclosed. These methods are compatible with various indoles ranging from electron-rich to -deficient substituents at the C-2, -5, -6, and -7-positions reacting with a series of different α-branched aldehydes. |
| Databáze: | OpenAIRE |
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