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Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels–Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone

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Abstract

Enantioselective dearomatization inverse-electron-demand Diels–Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone was realised using a chiral bisoxazoline/zinc complex as a catalyst. This transformation allowed for the synthesis of enantioenriched six-membered [2,3]-fused indolines (up to 99% yield and 88% ee).

Graphical abstract: Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels–Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone

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Article information


Submitted
28 Jan 2020
Accepted
05 Mar 2020
First published
05 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels–Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone

S. Zhao, S. Cheng, H. Liu, J. Zhang, M. Liu, W. Yuan and X. Zhang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00693A

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