Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/17935
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 
Issue Date: Sep-2006
Publisher: Elsevier
Serial title, monograph or event: Tetrahedron
Volume: 62
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. Graphical abstract
URI: http://hdl.handle.net/10316/17935
DOI: 10.1016/j.tet.2006.08.029
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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