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.
Marco Bandini, Elisabetta Manoni, Assunta De Nisi (2016). New opportunities in the stereoselective dearomatization of indoles. PURE AND APPLIED CHEMISTRY, 88(3), 207-214 [10.1515/pac-2016-0101].
New opportunities in the stereoselective dearomatization of indoles
BANDINI, MARCO;MANONI, ELISABETTA;DE NISI, ASSUNTA
2016
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
