Cyclopentanones—XIII: The proton donor depending stereoselectivity of lithium ammonia reduction of 2,3-dimethyl-4-hydroxy-2-cyclopentenone |
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| Authors: | M. Samson P. De Clerq M. Vandewalle |
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| Affiliation: | Department of Organic Chemistry, State University of Ghent, Laboratory of Organic Synthesis, Krijgslaan, 271(S4), B-9000 Gent, Belgium |
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| Abstract: | The stereochemistry of the lithium-liquid ammonia reduction of 2,3-dimethyl-4-hydroxy-2-cyclopentenone is discussed as a function of the acidity of the proton donor. It is shown that the configuration of the resulting 2,3-dimethyl-1,4-dihydroxycyclopentene is determined by competing intra- and intermolecular protonation. |
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