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Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles

Authors :
Artur M. S. Silva
Antonio M. d'A. Rocha Gonsalves
Agnieszka Kaczor
Teresa M. V. D. Pinho e Melo
Rui Fausto
Ana L. Cardoso
Source :
Repositório Científico de Acesso Aberto de Portugal, Repositório Científico de Acesso Aberto de Portugal (RCAAP), instacron:RCAAP
Publication Year :
2006
Publisher :
Elsevier, 2006.

Abstract

The 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate with nonstabilized azomethine ylides, generated via the decarboxylative condensation of 1,3-thiazolidine-4-carboxylic acids with aldehydes, afforded 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole derivatives. 2-Substituted-1,3-thiazolidine-4-carboxylic acids led to the stereoselective formation of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles. Quantum-chemistry calculations were carried out allowing the rationalization of the observed stereoselective formation of the anti-dipole. http://www.sciencedirect.com/science/article/B6THR-4KSSW69-5/1/f6fd75ae8164720ba1de8d3b3a44ed03

Details

Language :
English
Database :
OpenAIRE
Journal :
Repositório Científico de Acesso Aberto de Portugal, Repositório Científico de Acesso Aberto de Portugal (RCAAP), instacron:RCAAP
Accession number :
edsair.doi.dedup.....00265adf758b750dc91989ccf0448ff7