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How to control the chemoselectivity of the catalytic formation of chiral gamma-lactams or 2,3-disubstituted pyrroles by the choice of solvent

MONATSHEFTE FUR CHEMIE. Bd. 138. H. 7. 2007 S. 683 - 686

Erscheinungsjahr: 2007

ISBN/ISSN: 0026-9247

Publikationstyp: Zeitschriftenaufsatz

Doi/URN: 10.1007/s00706-007-0653-y

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Inhaltszusammenfassung


The reaction of the unsaturated imine methyl(3-phenylallylidene)amine with ethylene and carbon monoxide in the presence of catalytical amounts of Ru-3(CO)(12) leads to the formation of two heterocyclic products. One of the products is a chiral gamma-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 ...The reaction of the unsaturated imine methyl(3-phenylallylidene)amine with ethylene and carbon monoxide in the presence of catalytical amounts of Ru-3(CO)(12) leads to the formation of two heterocyclic products. One of the products is a chiral gamma-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. » weiterlesen» einklappen

Autoren


Gillies, Glenn (Autor)
Doennecke, Daniel (Autor)

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