New opportunities in the stereoselective dearomatization of indoles
Autor: | Marco Bandini, Elisabetta Manoni, Assunta De Nisi |
---|---|
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 |
Externí odkaz: |