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Title: 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: Cardoso, Ana L. 
Kaczor, Agnieszka 
Silva, Artur M. S. 
Fausto, Rui 
Melo, Teresa M. V. D. Pinho e 
Gonsalves, António M. d'A. Rocha 
Keywords: Azomethine ylides; 1,3-Dipolar cycloaddition; 1,3-Thiazolidine-4-carboxylic acids; 5,7a-Dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
Issue Date: 2006
Citation: Tetrahedron. 62:42 (2006) 9861-9871
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.
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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