New opportunities in the stereoselective dearomatization of indoles
| Autor: | Marco Bandini, Elisabetta Manoni, Assunta De Nisi |
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| Přispěvatelé: | Marco Bandini, Elisabetta Manoni, Assunta De Nisi |
| Rok vydání: | 2016 |
| Předmět: |
Brønsted acid
Indole test 010405 organic chemistry Chemistry General Chemical Engineering Enantioselective synthesis General Chemistry gold 010402 general chemistry 01 natural sciences dearomatization 0104 chemical sciences ESOC-19 indole Organic chemistry Stereoselectivity Brønsted–Lowry acid–base theory asymmetric catalysi |
| Zdroj: | Pure and Applied Chemistry. 88:207-214 |
| ISSN: | 1365-3075 0033-4545 |
| Popis: | The regio- and stereoselective dearomatization of indoles is realized for the first time by combining readily available indolyl precursors and electron-rich allenes, namely allenamides and aryloxyallenes. Inter- as well as intramolecular condensations were realized under gold and Brønsted acid catalysis providing a range of densely functionalized indoline and indolenine cores in high yields and excellent stereochemical outcome. Chemodivergent reaction profiles (Micheal-type addition vs. [2+2]-cycloaddition) were realized by a tailored design of both reaction conditions and functionalization of the reaction partners. |
| Databáze: | OpenAIRE |
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