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Issue 84, 2016
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Synthesis of polycyclic spiroindolines by highly diastereoselective interrupted Ugi cascade reactions of 3-(2-isocyanoethyl)indoles

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Abstract

We report a highly diastereoselective interrupted Ugi reaction to construct a broad range of structurally congested and stereochemically complex spiroindolines from tryptamine-derived isocyanides. The reaction is facilitated by using fluorinated alcohols (TFE or HFIP) as solvents and tolerates a broad range of amines, aldehydes and 2-isocyanoethylindoles to give polycyclic products in moderate to excellent yields.

Graphical abstract: Synthesis of polycyclic spiroindolines by highly diastereoselective interrupted Ugi cascade reactions of 3-(2-isocyanoethyl)indoles

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Publication details

The article was received on 12 Sep 2016, accepted on 23 Sep 2016 and first published on 26 Sep 2016


Article type: Communication
DOI: 10.1039/C6CC07459F
Citation: Chem. Commun., 2016,52, 12482-12485
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    Synthesis of polycyclic spiroindolines by highly diastereoselective interrupted Ugi cascade reactions of 3-(2-isocyanoethyl)indoles

    J. M. Saya, B. Oppelaar, R. C. Cioc, G. van der Heijden, C. M. L. Vande Velde, R. V. A. Orru and E. Ruijter, Chem. Commun., 2016, 52, 12482
    DOI: 10.1039/C6CC07459F

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