Furanose-based templates in the chemoselective generation of molecular diversity

Gómez, Ana M.; Uriel, Clara; López, J. Cristóbal

doi:10.1039/9781849734769-00376

Cited by 2 publications

(1 citation statement)

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“…On the other hand, our research group focused in an approach to appendage diversity consisting on "decorating" the carbohydrate moiety with additional functionalities that could be exploited in synthetic transfomations aimed at the formation of C-C, C-N, and C-O bonds [16,17]. In this context, we designed a furanose epoxy exo-glycal endowed with an exocyclic (enol-ether type) olefin and an oxirane moiety, i.e., 1 (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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

López

Lobo

Miranda

et al. 2014

Pure and Applied Chemistry

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Pyranosidic allylic (Ferrier) cations that share dicobalt hexacarbonyl propargyl (Nicholas) stabilization at C-1, can be easily generated by treatment of hexacarbonyldicobalt alkynyl glycals with BF 3 ·OEt 2 , 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-Cglycosides, containing two of such molecules.

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Section: Introductionmentioning

confidence: 99%