How to Control the Chemoselectivity of the Catalytic Formation of Chiral γ-Lactams or 2,3-Disubstituted Pyrroles by the Choice of Solvent |
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Authors: | Glenn Gillies Daniel Dönnecke Wolfgang Imhof |
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Institution: | Institut für Anorganische und Analytische Chemie der Friedrich-Schiller-Universit?t Jena, Jena, Germany
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Abstract: | Summary. The reaction of the unsaturated imine methyl(3-phenylallylidene)amine with ethylene and carbon monoxide in the presence of
catalytical amounts of Ru3(CO)12 leads to the formation of two heterocyclic products. One of the products is a chiral γ-lactam, the other one a 2,3-disubstituted
pyrrole derivative, in which only the carbon atom from carbon monoxide is incorporated. The selectivity in the formation of
the products may be controlled by the choice of solvent. In general, in nonpolar solvents the formation of the lactam is preferred
whereas the use of more polar solvents enhances the yield of the pyrrole. For most of the solvents used there is a linear
dependence of the product ratio on the relative permittivity of the corresponding solvent. Typically, polar aprotic solvents
do not follow this rule. |
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Keywords: | , C–,H Activation, Ruthenium, Lactams, Pyrroles, Solvent effects, |
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