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

Shu Mei Yang; Praneeth Karanam; Min Wang; Yeong Jiunn Jang; Yu Sheng Yeh; Ping Yao Tseng; Madhusudhan Reddy Ganapuram; Yan Cheng Liou; Wenwei Lin

doi:10.1039/c8cc09219b

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

Shu Mei Yang, Praneeth Karanam, Min Wang, Yeong Jiunn Jang, Yu Sheng Yeh, Ping Yao Tseng, Madhusudhan Reddy Ganapuram, Yan Cheng Liou, Wenwei Lin

Department of Chemistry

Research output: Contribution to journal › Article

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1398-1401
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	10
DOIs	https://doi.org/10.1039/c8cc09219b
Publication status	Published - 2019 Jan 1

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ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Cite this

Yang, S. M., Karanam, P., Wang, M., Jang, Y. J., Yeh, Y. S., Tseng, P. Y., Ganapuram, M. R., Liou, Y. C., & Lin, W. (2019). A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters. Chemical Communications, 55(10), 1398-1401. https://doi.org/10.1039/c8cc09219b

A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters. / Yang, Shu Mei; Karanam, Praneeth; Wang, Min; Jang, Yeong Jiunn; Yeh, Yu Sheng; Tseng, Ping Yao; Ganapuram, Madhusudhan Reddy; Liou, Yan Cheng; Lin, Wenwei.

In: Chemical Communications, Vol. 55, No. 10, 01.01.2019, p. 1398-1401.

Research output: Contribution to journal › Article

Yang, Shu Mei ; Karanam, Praneeth ; Wang, Min ; Jang, Yeong Jiunn ; Yeh, Yu Sheng ; Tseng, Ping Yao ; Ganapuram, Madhusudhan Reddy ; Liou, Yan Cheng ; Lin, Wenwei. / A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters. In: Chemical Communications. 2019 ; Vol. 55, No. 10. pp. 1398-1401.

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10.1039/c8cc09219b