Document Type : Short communication
Authors
1 Department of Chemistry, Imam Hossein University, PB BOX 995-16765 Tehran, Iran
2 Department of Chemistry, Shahid Beheshti University, PB BOX 1983963113 Tehran, Iran
Abstract
An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/pyrrolizidines with highly regio- and diastereo-enantio, selective from 1,3-dipolar cycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the reaction is discussed on basis of the assignment of the absolute configuration of one of the cycloaddition products, which obtained by single crystal X-ray analysis. The process occurs at reflux temperature in ethanol as green solvent and in the absence of any bidentate chelating Lewis acids. Functionalized pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds.1 Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems.
Graphical Abstract
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Keywords
- Chiral spiro oxindolopyrrolidines
- pyrrolizidines
- azomethine ylides
- chiral menthol-drived trans-cinnamic
- isatin
- sarcosine
Main Subjects
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