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Decarboxylative-Mediated Regioselective 1,3-Dipolar Cycloaddition for Diversity-Oriented Synthesis of Structurally exo ′-Selective Spiro[oxindole-pyrrolidine-dihydrocoumarin] Hybrids.
- Source :
-
Synthesis . 2020, Vol. 52 Issue 20, p3018-3028. 11p. - Publication Year :
- 2020
-
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--i-ndole-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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00397881
- Volume :
- 52
- Issue :
- 20
- Database :
- Academic Search Index
- Journal :
- Synthesis
- Publication Type :
- Academic Journal
- Accession number :
- 146172127
- Full Text :
- https://doi.org/10.1055/s-0040-1707895