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A substrate-based approach to skeletal diversity from dicobalt hexacarbonyl (C1)-alkynyl glycals by exploiting its combined ferrier-nicholas reactivity

AuthorsLobo, Fernando ; Gómez, Ana M. ; Miranda, Silvia; López, J. Cristobal
KeywordsFerrier reaction
Nicholas reaction
Synthesis design
Synthetic methods
Issue Date2014
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 20: 10492- 10502 (2014)
AbstractNovel 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.
Identifiersdoi: 10.1002/chem.201402149
issn: 0947-6539
e-issn: 1521-3765
Appears in Collections:(IQOG) Artículos
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