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Issue 15, 2018
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A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines

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Abstract

We report a Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles and indole-derived ketimines to rapidly afford hexacyclic spiroindolines featuring three stereocenters including two quaternary stereocenters in moderate to excellent yields (30–89%) with complete diastereoselectivity. This reaction is highly efficient because two C–C and one C–N bonds as well as two new rings are created under mild reaction conditions in a single step.

Graphical abstract: A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines

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Publication details

The article was received on 13 Apr 2018, accepted on 08 Jun 2018 and first published on 08 Jun 2018


Article type: Research Article
DOI: 10.1039/C8QO00382C
Citation: Org. Chem. Front., 2018,5, 2303-2307

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    A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines

    Y. Liu, X. Mao, X. Lin and G. Chen, Org. Chem. Front., 2018, 5, 2303
    DOI: 10.1039/C8QO00382C

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