The behaviour of 4-hydroxy-4-methylcyclopent-2-enone and related 4-substituted cyclopent-2-enones towards 1,3-dipolar cycloaddition with nitrile oxides is studied.The reactions are always completely regioselective while the diastereofacial selectivity depends on the nature of the substituents. Remarkably, the reaction of 4-acetoxycyclopent2-enone shows complete regio- and diastereo-facial selectivity. © The Royal Society of Chemistry 2000.
Adembri, G., Giorgi, G., Lampariello, R.L., Paoli, M.L., Sega, A. (2000). Regio-and Diastereo-Selectivity in 1,3-Dipolar Cycloadditions of Nitrile Oxides to 4-Substituted Cyclopent-2-enones. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1(16), 2649-2656 [10.1039/b003549l].
Regio-and Diastereo-Selectivity in 1,3-Dipolar Cycloadditions of Nitrile Oxides to 4-Substituted Cyclopent-2-enones
Adembri G.;Giorgi G.;Lampariello R. L.;Sega A.
2000-01-01
Abstract
The behaviour of 4-hydroxy-4-methylcyclopent-2-enone and related 4-substituted cyclopent-2-enones towards 1,3-dipolar cycloaddition with nitrile oxides is studied.The reactions are always completely regioselective while the diastereofacial selectivity depends on the nature of the substituents. Remarkably, the reaction of 4-acetoxycyclopent2-enone shows complete regio- and diastereo-facial selectivity. © The Royal Society of Chemistry 2000.
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https://hdl.handle.net/11365/33219
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