Highly Efficient, Catalyst-Free, Diastereoselective, Diversity-Oriented Synthesis of Dihydrocoumarin–Pyrrolidine–Spirooxindoles Bearing Three Contiguous Stereocenters

Xiong Zuo; Shuang Chen; Sheng-Wen Xu; Shun-Qin Chang; Xiong-Li Liu; Ying Zhou; Wei-Cheng Yuan

doi:10.1055/s-0037-1610875

Synthesis, Table of Contents

Synthesis 2019; 51(11): 2339-2350
DOI: 10.1055/s-0037-1610875

paper

Highly Efficient, Catalyst-Free, Diastereoselective, Diversity-Oriented Synthesis of Dihydrocoumarin–Pyrrolidine–Spirooxindoles Bearing Three Contiguous Stereocenters

Xiong Zuo

^aGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Shuang Chen

^aGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Sheng-Wen Xu

^aGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Shun-Qin Chang

^aGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Xiong-Li Liu *

^aGuizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Ying Zhou

^bCollege of Pharmaceutical Sciences, Guizhou University of Chinese Medicine, Guiyang, Guizhou 550025, P. R. of China

,

Wei-Cheng Yuan

^cKey Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China

› Author Affiliations

Abstract

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Abstract

A new methodology has been developed for the highly efficient diastereoselective construction of dihydrocoumarin–pyrrolidine–spirooxindole collections via a domino Michael/annulation reaction of 3-isothiocyanato oxindoles and coumarins under catalyst-free conditions. The resulting biologically important molecules bearing three pharmacophores and three contiguous stereocenters were obtained in up to 92% yield and >20:1 dr. It is noteworthy that utilization of a carboxylic acid activation/decarboxylation strategy represents an efficient approach for the domino Michael/annulation reaction of the chemically inert coumarin moiety. This protocol could expand candidate libraries, that will benefit the requirement for new bioactive molecules.

Key words

dihydrocoumarins - pyrrolidines - spirooxindoles - 3-isothiocyanato oxindoles - catalyst-free

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References

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