Decarboxylative-Mediated Regioselective 1,3-Dipolar Cycloaddition for Diversity-Oriented Synthesis of Structurally exo′-Selective Spiro[oxindole-pyrrolidine-dihydrocoumarin] Hybrids

Xiong-Wei Liu; Shun-Qin Chang; Qi-Lin Wang; Shuang Chen; Jun-Xin Wang; Wei Zhou; Ying Zhou

doi:10.1055/s-0040-1707895

Synthesis, Table of Contents

Synthesis 2020; 52(20): 3018-3028
DOI: 10.1055/s-0040-1707895

paper

Decarboxylative-Mediated Regioselective 1,3-Dipolar Cycloaddition for Diversity-Oriented Synthesis of Structurally exo′-Selective Spiro[oxindole-pyrrolidine-dihydrocoumarin] Hybrids

Xiong-Wei Liu

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

,

Shun-Qin Chang

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

Qi-Lin Wang

^cInstitute of Functional Organic Molecular Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, P. R. of China Email: zhouy@gzu.edu.cn

,

Shuang Chen

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

Jun-Xin Wang

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

Wei Zhou

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

Ying Zhou∗

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

› Author Affiliations

Abstract

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Abstract

A general and practical three-component regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins has been developed. This reaction displayed good substrate tolerance and gave a diverse array of biologically relevant spiro[ox-indole-pyrrolidine-dihydrocoumarin] derivatives bearing four contiguous stereocenters including one spiro quaternary center in moderate to high yields (up to 90%) with high diastereoselectivities (up to 15:1 dr). It is based on the application of carboxylic acid activated coumarins as dienophiles followed by a decarboxylation process. The possible mechanism of the 1,3-dipolar cycloaddition is proposed via an exo′-transition state. Furthermore, this is the first example of decarboxylative-mediated regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins.

Key words

decarboxylative - regioselective - 1,3-dipolar cycloaddition - diversity-oriented synthesis - multiple pharmacore molecules

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References

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