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A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

Author:
Yang, Shu-Mei, Karanam, Praneeth, Wang, Min, Jang, Yeong-Jiunn, Yeh, Yu-Sheng, Tseng, Ping-Yao, Ganapuram, Madhusudhan Reddy, Liou, Yan-Cheng, Lin, Wenwei
Source:
Chemical communications 2019 v.55 no.10 pp. 1398-1401
ISSN:
1364-548X
Subject:
catalytic activity, chemical communication, chemical compounds, chemical reactions, enantioselectivity
Abstract:
An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene oxindoles to fully substituted enones and demonstrates the usefulness of the latter as efficient Michael acceptors in generating complex caged products in 26–92% yields, 14–98% ee and up to >25 : 1 d.r. values.
Agid:
6287778