Cyclopentanones—XVIII : The lithium-liquid ammonia reduction of some 2,3-dialkyl-(4-hydroxy)-2-cyclopentenones. the importance of the protonation of intermediate enolate anions on the stereochemical outcome |
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| Authors: | M. Samson P. De Clercq M. Vandewalle |
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| Affiliation: | Department of Organic Chemistry, State University of Ghent, Laboratory for Organic Synthesis, Krijgslaan, 271 (S 4), B-9000 Gent, Belgium |
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| Abstract: | The stereochemical outcome of the lithium-liquid ammonia reduction of 2,3-dialkyl-4-hydroxy-2-cyclopentenones and 2,3-dialkyl-2-cyclopentenones possessing bulky substituents (i-propyl and t-butyl) is investigated, using different proton donors. The relative configuration of both alkyl groups in the reduction products is interpreted on the basis of the geometry of the transition state for protonation of the intermediate enolate anions formed during the reduction |
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