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Asymmetric catalysis, CIII: EnantioselectiveMichael addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes

Asymmetrische Katalyse, 103. Mitt.: EnantioselektiveMichael-Addition von 1,3-Dicarbonylverbindungen an konjugierte Nitroalkene

  • Organische Chemie Und Biochemie
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Summary

Optically activeMichael adducts were synthesized by addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes. Good chemical yields were obtained for nitroalkenes stabilized by an aromatic substituent without any further substituents at the double bond. Acetylacetone and methyl-2,3-dihydro-1-oxo-1H-indene-2-carboxylate were used asMichael donors and four cinchona alkaloids as chiral base catalysts. Enantiomeric excess determinations were performed by1H NMR spectroscopy in the presence of thePirkle alcohol and by HPLC on chiral stationary phases. A correlation between the relative configuration of the prevailing isomer of theMichael adduct and the catalysts was established.

Zusammenfassung

Optisch aktiveMichael-Addukte werden durch die Addition von 1,3-Dicarbonylverbindungen an konjugierte Nitroalkene synthetisiert. Gute chemische Ausbeuten werden für durch aromatische Substituenten stabilisierte Nitroalkene ohne weitere Substituenten an der Doppelbindung erreicht. Acetylaceton und 2,3-Dihydro-1-oxo-1H-inden-2-carbonsäuremethylester werden alsMichael-Donoren und vier Cinchona-Alkaloide als chirale basische Katalysatoren verwendet. Die Bestimmung des Enantiomerenüberschusses wird mittels1H-NMR-Spektroskopie in Gegenwart vonPirkle-Alkohol und HPLC an chiralen stationären Phasen durchgeführt. Eine Korrelation zwischen der relativen Konfiguration der Vorzugsisomeren derMichael-Addukte und den Katalysatoren wurde hergestellt.

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Authors and Affiliations

  1. Institut für Anorganische Chemie, Universität Regensburg, D-93040, Regensburg, Deutschland

    H. Brunner & B. Kimel

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  1. H. Brunner
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  2. B. Kimel
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Brunner, H., Kimel, B. Asymmetric catalysis, CIII: EnantioselectiveMichael addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes. Monatsh Chem 127, 1063–1072 (1996). https://doi.org/10.1007/BF00807579

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  • DOI: https://doi.org/10.1007/BF00807579

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