Gold‐Catalyzed Regioselective Tetradehydro‐Diels‐Alder Reaction of Yne‐Ynamides: Access to 2,3‐Dihydrobenzo[ f ]indoles

Prabagar, B. ; Dutta, Shubham ; Gandon, Vincent ; Sahoo, Akhila K. (2019) Gold‐Catalyzed Regioselective Tetradehydro‐Diels‐Alder Reaction of Yne‐Ynamides: Access to 2,3‐Dihydrobenzo[ f ]indoles Asian Journal of Organic Chemistry, 8 (7). pp. 1128-1132. ISSN 2193-5807

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Official URL: http://doi.org/10.1002/ajoc.201900225

Related URL: http://dx.doi.org/10.1002/ajoc.201900225

Abstract

Presented herein is a gold(I) catalyzed intramolecular tetradehydro-Diels-Alder (TDDA) reaction of alkyne-tethered-ynamides for the construction of structurally complex 2,3-dihydrobenzo[f]indole derivatives. The mechanism of the regioselective benzannulation reaction was rationalized by means of density functional theory (DFT) calculations. Substrates having an aryl group at the ynamide terminus are exclusively participating in this TDDA reaction under gold catalysis.

Item Type:Article
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ID Code:121777
Deposited On:22 Jul 2021 07:21
Last Modified:22 Jul 2021 07:21

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