A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines. Issue 15 (14th June 2018)

• Record Type: Journal Article
• Authors: Liu, Yun-Lin; Mao, Xiang-Yu; Lin, Xiao-Tong; Chen, Guo-Shu
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 15(2018)
• Page Start: 2303
• Page End: 2307
• Publication Date: 2018-06-14
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00382c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles and indole-derived ketimines was developed for the synthesis of hexacyclic spiroindolines featuring three stereocenters including two quaternary stereocenters. 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.