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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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Article information


Submitted
12 Sep 2016
Accepted
23 Sep 2016
First published
26 Sep 2016

Chem. Commun., 2016,52, 12482-12485
Article type
Communication

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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