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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.

Nitrile oxide cycloaddition to 4-hydroxy-2-cyclopentenone: Solvent effect and selectivity

FASSARDI, VERA;BASILE, TERESA;MEMEO, MISAL GIUSEPPE;QUADRELLI, PAOLO
2017-01-01

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.
2017
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
TETRAHEDRON LETTERS
sì
2-s2.0-85025099852
Esperti anonimi
Inglese
Internazionale
STAMPA
58
34
3385
3389
5
4-Hydroxy-2-cyclopentenone; Nitrile oxide; Nucleoside synthesis; Solvent effect; Stereoselectivity; Biochemistry; Drug Discovery3003 Pharmaceutical Science; Organic Chemistry
http://www.journals.elsevier.com/tetrahedron-letters/
no
4
info:eu-repo/semantics/article
262
Fassardi, Vera; Basile, Teresa; Memeo, MISAL GIUSEPPE; Quadrelli, Paolo
1 Contributo su Rivista::1.1 Articolo in rivista
none
1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/1187308
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