Intermolecular cycloaddition of nonstabilized azomethine ylides generated from ...

• Author(s): Cardoso, Ana L. ; Kaczor, Agnieszka ; Silva, Artur M. S. ; Fausto, Rui ; Melo, Teresa M. V. D. Pinho e ; Gonsalves, António M. d'A. Rocha
• Date: 2006
• Persistent ID: http://hdl.handle.net/10316/5070
• Origin: Estudo Geral - Universidade de Coimbra
• Subject(s): Azomethine ylides; 1,3-Dipolar cycloaddition; 1,3-Thiazolidine-4-carboxylic acids; 5,7a-Dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
• Document Type: Article
• Language: English

Description

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