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 / Marco Bandini; Elisabetta Manoni; Assunta De Nisi. - In: PURE AND APPLIED CHEMISTRY. - ISSN 0033-4545. - STAMPA. - 88:3(2016), pp. 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.
2016
New opportunities in the stereoselective dearomatization of indoles / Marco Bandini; Elisabetta Manoni; Assunta De Nisi. - In: PURE AND APPLIED CHEMISTRY. - ISSN 0033-4545. - STAMPA. - 88:3(2016), pp. 207-214. [10.1515/pac-2016-0101]
Marco Bandini; Elisabetta Manoni; Assunta De Nisi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/545982
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