Data di Pubblicazione:
2017
Abstract:
The facial selectivity in the nitrile oxide cycloaddition reactions of 4-hydroxy-2-cyclopentenone and its
bulky t-butyloxy derivative is reported. A quantitative evaluation of the solvent effect on the hydrogen
bonding directing ability is given, showing the presence of some syn-stereoselectivity even in good
H-bond acceptor solvents. The stereoselectivities of the O-t-butyl derivative may serve as reference data
for more complex systems and point to the existence of a sole steric effect on the directivity; M(II) ions
did not significantly improve the selectivity. The results are also discussed in light of the potential
application of these scaffolds in the nucleoside analogue synthesis.
bulky t-butyloxy derivative is reported. A quantitative evaluation of the solvent effect on the hydrogen
bonding directing ability is given, showing the presence of some syn-stereoselectivity even in good
H-bond acceptor solvents. The stereoselectivities of the O-t-butyl derivative may serve as reference data
for more complex systems and point to the existence of a sole steric effect on the directivity; M(II) ions
did not significantly improve the selectivity. The results are also discussed in light of the potential
application of these scaffolds in the nucleoside analogue synthesis.
Tipologia CRIS:
1.1 Articolo in rivista
Keywords:
4-Hydroxy-2-cyclopentenone; Nitrile oxide; Nucleoside synthesis; Solvent effect; Stereoselectivity; Biochemistry; Drug Discovery3003 Pharmaceutical Science; Organic Chemistry
Elenco autori:
Fassardi, Vera; Basile, Teresa; Memeo, MISAL GIUSEPPE; Quadrelli, Paolo
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