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Synthesis 2020; 52(20): 3018-3028
DOI: 10.1055/s-0040-1707895
paper
© Georg Thieme Verlag Stuttgart · New York

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

Xiong-Wei Liu
a   College of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P. R. of China
,
Shun-Qin Chang
b   Guizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China
,
Qi-Lin Wang 
c   Institute 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
b   Guizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China
,
Jun-Xin Wang
b   Guizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China
,
Wei Zhou
b   Guizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China
,
Ying Zhou∗
a   College of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P. R. of China
› Author AffiliationsWe are grateful for the financial support from the NSFC (81660576), Project of Guizhou Province ([2020]1Y396, [2019]1402, and [2015]4032) and Doctoral Project of Guizhou University of Traditional Chinese Medicine ([2019]05).
Further Information

Publication History

Received: 15 February 2020

Accepted after revision: 02 June 2020

Publication Date:
09 July 2020 (online)

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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

Supporting Information

 

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