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Diastereoselective construction of 3-aryl-substituted indolines via annulation of in situ generated p-quinone methides

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Abstract

A highly diastereoselective [4 + 1] annulation reaction of in situ generated p-quinone methides for the synthesis of 3-aryl-substituted indolines has been developed. Employing commercial manganese dioxide as the oxidant, a series of ortho-tosylaminophenyl-substituted p-QMs could be generated in situ. This new protocol is based on an unprecedented 1,6-conjugate addition/annulation cascade reaction, without the need for pre-synthesized p-QMs, and enables the easy preparation of a variety of 3-aryl-2,3-dihydroindoles in good to excellent yields.

Graphical abstract: Diastereoselective construction of 3-aryl-substituted indolines via annulation of in situ generated p-quinone methides

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Publication details

The article was received on 31 Oct 2019, accepted on 13 Nov 2019 and first published on 15 Nov 2019


Article type: Communication
DOI: 10.1039/C9OB02351H
Org. Biomol. Chem., 2019, Advance Article

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    Diastereoselective construction of 3-aryl-substituted indolines via annulation of in situ generated p-quinone methides

    J. Wang, X. Pan, L. Zhao, L. Zhao, J. Liu, Y. Zhi, A. Wang, K. Zhao and L. Hu, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB02351H

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