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Ferrier-Nicholas pyranosidic cations: application to diversity-oriented synthesis

AuthorsLópez, J. Cristobal; Lobo, Fernando ; Miranda, Silvia; Uriel, Clara ; Gómez, Ana M.
KeywordsDiversity-oriented synthesis
Stereocontrolled synthesis
Pyranosidic cations
Nicholas reaction
Tandem reactions
Ferrrier reaction
Issue Date2014
PublisherMarcel Dekker
CitationJournal of Macromolecular Science - Pure and Applied Chemistry 86: 1357-1364 (2014)
AbstractPyranosidic allylic (Ferrier) cations that share dicobalt hexacarbonyl propargyl (Nicholas) stabilization at C-1, can be easily generated by treatment of hexacarbonyldicobalt alkynyl glycals with BF3,OEt2, and display a remarkable reactivity leading to a variety of products. The substituent at O-6 in these glycals plays a pivotal role in directing the outcome of the transformations. Accordingly, 6-O-benzyl or 6-O-allyl groups cause a series of transformations resulting in the stereoselective formation of oxepanes through a process that involves an initial hydride transfer step from the allyl or benzyl substituent to the Ferrier-Nicholas cation. On the contrary, 6-OH derivatives undergo an overall ring contraction to branched tetrahydrofuran derivatives. 6-O-Silyl derivatives, in the presence of heteroaryl nucleophiles, were transformed into C-3 branched bis-C-C-glycosides, containing two of such molecules.
Identifiersdoi: 10.1515/pac-2014-0402
issn: 1060-1325
e-issn: 1520-5738
Appears in Collections:(IQOG) Artículos
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