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… Click to show full abstract
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.
Journal Title: Tetrahedron Letters
Year Published: 2017
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