Issue 15, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
13 Apr 2018
Accepted
08 Jun 2018
First published
08 Jun 2018

Org. Chem. Front., 2018,5, 2303-2307

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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