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Stereochemical differences in the michael addition of phenylacetic acid esters and dialkyl amides to methyl cinnamate or methyl crotonate

Stereochemische Unterschiede bei der Michael Addition von Phenylessig-Estern und -Dialkylamiden an Methylcinnamat oder Methylcrotonat

  • Organische Chemie Und Biochemie
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Summary

The stereochemistry of the conjugate addition of phenylacetic acid esters and dialkylamides to methyl crotonate is studied. The stereochemical results are compared with these previously obtained for the addition to methyl cinnamate. The differences observed are explained in terms of cyclic transition states with decreasing of the sterical interactions as a result of replacement of a phenyl group by methyl in position 2 of the 1,2-diphenylpropanic skeleton.

Zusammenfassung

Es wird die Stereochemie der Addition von Phenylessig-ester und der-dialkylamide an Methylcrotonat untersucht. Die stereochemischen Ergebnisse werden mit den früher publizierten für die Addition an Methylcinnamat verglichen. Die beobachteten Unterschiede werden mit der abnehmenden sterischen Wechselwirkung beim Austausch von Phenyl gegen Methyl am C-2 des 1,2-Diphenylpropan-Skeletts unter der Voraussetzung eines cyclischen Übergangszustandes erklärt.

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Authors and Affiliations

  1. Institute of Organic Chemistry with Center of Phytochemistry, Bulgarian Academy of Sciences, 1113, Sofia, Bulgaria

    T. S. Gospodova & Y. N. Stefanovsky

Authors
  1. T. S. Gospodova
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  2. Y. N. Stefanovsky
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Gospodova, T.S., Stefanovsky, Y.N. Stereochemical differences in the michael addition of phenylacetic acid esters and dialkyl amides to methyl cinnamate or methyl crotonate. Monatsh Chem 125, 217–223 (1994). https://doi.org/10.1007/BF00818166

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  • DOI: https://doi.org/10.1007/BF00818166

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