DOI: 10.1039/A807678B
(Paper)
J. Chem. Soc., Perkin Trans. 1, 1999, 1219-1224
Intramolecular dipolar cycloaddition reaction of 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates: synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives
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Teresa M. V. D. Pinho e Melo, Dália M. Barbosa, Paulo J. R. S. Ramos, António M. d’A. Rocha Gonsalves, Thomas L. Gilchrist, Ana M. Beja, José A. Paixão, Manuela R. Silva and Luiz Alte da Veiga
Abstract
(2R,4R)-N-Acyl-2-phenylthiazolidine-4-carboxylic acids were used to generate 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates with internal dipolarophiles. The intramolecular 1,3-dipolar cycloaddition of these mesoionic species led to the synthesis of new 1H-pyrrolo[1,2-c]thiazole derivatives (8a, 8b and 12) as single enantiomers. The structure of 8a was determined by X-ray crystallography.