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

Research output: Contribution to journal › Article

3 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 languageEnglish
Pages (from-to)1398-1401
Number of pages4
JournalChemical Communications
Volume55
Issue number10
DOIs
Publication statusPublished - 2019 Jan 1

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Bearings (structural)
Scaffolds
oxindole

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

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, SM, Karanam, P, Wang, M, Jang, YJ, Yeh, YS, Tseng, PY, Ganapuram, MR, Liou, YC & Lin, W 2019, 'A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters', Chemical Communications, vol. 55, no. 10, pp. 1398-1401. https://doi.org/10.1039/c8cc09219b
Yang SM, Karanam P, Wang M, Jang YJ, Yeh YS, Tseng PY et al. A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters. Chemical Communications. 2019 Jan 1;55(10):1398-1401. https://doi.org/10.1039/c8cc09219b
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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