Synthesis 2019; 51(03): 683-692
DOI: 10.1055/s-0037-1610290
paper
© Georg Thieme Verlag Stuttgart · New York

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

a   School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Sichuan Zigong 64300, P. R. of China
b   Guizhou 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 §
b   Guizhou 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*
a   School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Sichuan Zigong 64300, P. R. of China
,
Sheng-Wen Xu
b   Guizhou 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
b   Guizhou 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
b   Guizhou 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*
b   Guizhou 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
› Author Affiliations
We are grateful for the financial support from the National Natural Science Foundations of China (No. 81560563, No. 81760625, and No. 21402132); Project of Guizhou province (Qian Ke He Zi [2016]5623, Qian Ke He Zi [2017]5609, Qian Ke He G Z [2015]4001, and Qian Jiao Yan He JG Zi [2016]06).
Further Information

Publication History

Received: 21 July 2018

Accepted after revision: 31 August 2018

Publication Date:
24 September 2018 (online)


§ 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.

Supporting Information