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Synthesis 2013; 45(16): 2294-2304
DOI: 10.1055/s-0033-1338492
DOI: 10.1055/s-0033-1338492
paper
Synthesis of Functionalized Pyrrolizidines/Pyrrolidines Incorporating a Spirooxindole Motif through [3+2] Cycloaddition
Further Information
Publication History
Received: 26 February 2013
Accepted after revision: 20 May 2013
Publication Date:
09 July 2013 (online)
Abstract
Dimethyl 2-(aryloxy)fumarates and dimethyl 2-(alkyl- or arylthio)fumarates are shown to be efficient dipolarophiles in 1,3-dipolar cycloaddition reaction with azomethine ylides, which are generated by the reaction of isatin with the secondary amino acids proline or sarcosine. In these reactions, dimethyl 2-(alkyl- or arylthio)fumarates afforded spirooxindolopyrrolizidines or -pyrrolidines in high yields with excellent regioselectivities, while dimethyl 2-(aryloxy)fumarates produced mixtures of regioisomers. DFT calculations at the B3LYP/6-31G(d,p) level were consistent with the observed results. Tri- and tetracyclic compounds were obtained through regio- and stereoselective intramolecular cycloaddition of O-vinylic salicylaldehyde with secondary amino acids.
Key words
2-(aryloxy)fumarates - 2-(alkyl- or arylthio)fumarates - azomethine ylides - spiro compounds - pyrrolizidines - pyrrolidines - DFT calculationsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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