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

被引：4

作者：

Fassardi, Vera ^{[1
]}

Basile, Teresa ^{[1
]}

Memeo, Misal Giuseppe ^{[1
]}

Quadrelli, Paolo ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim, Viale Taramelli 12, I-27100 Pavia, Italy

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 34期

关键词：

Nitrile oxide; 4-Hydroxy-2-cyclopentenone; Solvent effect; Stereoselectivity; Nucleoside synthesis; 1,3-DIPOLAR CYCLOADDITIONS; ACCELERATION; ALPHA; BETA;

D O I：

10.1016/j.tetlet.2017.07.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：3385 / 3389

页数：5

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