Highly Diastereo-, α-Regioselective Catalyst-Free Construction of Adjacent Dispirobisoxindoles with Three Contiguous Quaternary Carbon Centers

Xiong-Li Liu; Shun-Qin Chang; Yan Jiang; Sheng-Wen Xu; Xiong Zuo; Shuang Chen; Min-Yi Tian

doi:10.1055/s-0037-1610290

Synthesis, Table of Contents

Synthesis 2019; 51(03): 683-692
DOI: 10.1055/s-0037-1610290

paper

Highly Diastereo-, α-Regioselective Catalyst-Free Construction of Adjacent Dispirobisoxindoles with Three Contiguous Quaternary Carbon Centers

Xiong-Li Liu §

^aSchool of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Sichuan Zigong 64300, P. R. of China

^bGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang 550025, P. R. of China Email: mytian@gzu.edu.cn Email: zhongyaominzuyao@163.com

,

Shun-Qin Chang §

^bGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang 550025, P. R. of China Email: mytian@gzu.edu.cn Email: zhongyaominzuyao@163.com

,

Yan Jiang*

^aSchool of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Sichuan Zigong 64300, P. R. of China

,

Sheng-Wen Xu

^bGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang 550025, P. R. of China Email: mytian@gzu.edu.cn Email: zhongyaominzuyao@163.com

,

Xiong Zuo

^bGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang 550025, P. R. of China Email: mytian@gzu.edu.cn Email: zhongyaominzuyao@163.com

,

Shuang Chen

^bGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang 550025, P. R. of China Email: mytian@gzu.edu.cn Email: zhongyaominzuyao@163.com

,

Min-Yi Tian*

^bGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang 550025, P. R. of China Email: mytian@gzu.edu.cn Email: zhongyaominzuyao@163.com

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Abstract

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^§ These two authors contributed equally to this work

Abstract

A new methodology was developed for the highly diastereoselective construction of dispirobisoxindole scaffolds via a domino α-regioselective Michael/cyclization reaction sequence of 3-isothiocyanato oxindoles and isatylidene malononitriles under catalyst-free conditions. Complex polycyclic oxindoles featuring two side-by-side oxindole skeletons and three contiguous quaternary carbon centers were synthesized in up to 95% yield and >20:1 dr. This protocol could provide libraries of stereochemically rich small molecules that will help in the search for new bioactive molecules.

Key words

3-isothiocyanato oxindoles - quaternary carbon center - diastereoselective - α-regioselective - catalyst-free

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10a CCDC 1855873, 1855874, 1855875, 1855876, 1855877, 1855878, 1855879, and 1855881 contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
10b For other crystallographic data, see the Supporting Information.

Supplementary Material

Supporting Information