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Título: | A substrate-based approach to skeletal diversity from dicobalt hexacarbonyl (C1)-alkynyl glycals by exploiting its combined ferrier-nicholas reactivity |
Autor: | Lobo, Fernando CSIC; Gómez, Ana M. CSIC ORCID ; Miranda, Silvia CSIC; López, J. Cristóbal | Palabras clave: | Ferrier reaction Glycals Nicholas reaction Synthesis design Synthetic methods |
Fecha de publicación: | 2014 | Editor: | John Wiley & Sons | Citación: | Chemistry - A European Journal 20: 10492- 10502 (2014) | Resumen: | Novel substrates that combine dicobalt hexacarbonyl propargyl (Nicholas) and pyranose-derived allylic (Ferrier) cations have been generated by treatment of hexacarbonyldicobalt (C-1)-alkynyl glycals with BF3 .Et2O. The study of these cations has resulted in the discovery of novel reaction pathways that have shown to be associated to the nature of O-6 substituent in the starting alkynyl glycals. Accordingly, compounds resulting from ring expansion (oxepanes), ring contraction (tetrahydrofurans), or branched pyranoses, by incorporation of nucleophiles, can be obtained from 6-O-benzyl, 6-hydroxy, or 6-O-silyl derivatives, respectively. The use of a 6-O-allyl alkynyl glycal led to a suitable funtionalized oxepane able to experience an intramolecular Pauson-Khand cyclization leading to a single tricyclic derivative. | URI: | http://hdl.handle.net/10261/102102 | DOI: | 10.1002/chem.201402149 | Identificadores: | doi: 10.1002/chem.201402149 issn: 0947-6539 e-issn: 1521-3765 |
Aparece en las colecciones: | (IQOG) Artículos |
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