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Issue 23, 2018
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Organocatalytic asymmetric synthesis of tetrahydrocarbazoles via an inverse-electron-demand Diels–Alder reaction of 2,3-indole-dienes with enals

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Abstract

A novel 2,3-indole-diene synthon was designed and synthesized, and was first applied to a stereoselective inverse-electron-demand Diels–Alder reaction to construct tetrahydrocarbazoles. In the presence of chiral secondary amines, a variety of enantioenriched, multifunctionalized tetrahydrocarbazole derivatives were obtained in good yields (up to 83%) with excellent stereoselectivities (up to >20 : 1 dr, 98% ee).

Graphical abstract: Organocatalytic asymmetric synthesis of tetrahydrocarbazoles via an inverse-electron-demand Diels–Alder reaction of 2,3-indole-dienes with enals

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Publication details

The article was received on 26 Sep 2018, accepted on 17 Oct 2018 and first published on 23 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO01042K
Citation: Org. Chem. Front., 2018,5, 3430-3434
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    Organocatalytic asymmetric synthesis of tetrahydrocarbazoles via an inverse-electron-demand Diels–Alder reaction of 2,3-indole-dienes with enals

    B. Gu, W. Yang, S. Wu, Y. Wang and W. Deng, Org. Chem. Front., 2018, 5, 3430
    DOI: 10.1039/C8QO01042K

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