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.
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.File in questo prodotto:
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