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Addition von enantiomerenreinen Aminen an aktivierte Olefine, 2. Mitt. Über die Addition an (E)-4-Oxo-4-phenyl-2-butensäure-ethylester

Addition of Enantiomerically Pure Amines to Activated Olefines II. On the Addition to Ethyl (E)-4-Oxo-4-phenyl-2-butenoate

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Zusammenfassung.

 Die Addition von (S)-Phenethylamin an (E)-4-Oxo-4-phenyl-2-butensäureethylester verläuft ohne kinetische Selektivität. Addiert man hingegen (S)-Alaninisopropylester beziehungsweise benzylester, ist das nach der b,pl,H-Regel als AB- beziehungsweise BB-Produkt zu bezeichnende Diastereomere kinetisch bevorzugt. Bei der Addition von (S)-Alaninbenzylester ist im Unterschied zu den anderen und früher untersuchten Beispielen das BB-Produkt gegenüber dem AB-Produkt thermodynamisch nicht bevorzugt.

Summary.

 The addition of (S)-phenethylamine to ethyl (E)-4-oxo-4-phenyl-2-butenoate shows no kinetic selectivity, whereas – according to the b,pl,H-rule – the AB- and BB-product are kinetically preferred in the addition of (S)-alanine-isopropylester and -benzylester, respectively. In the reaction of benzyl (S)-alaninate, contrary to the other and earlier examined examples no thermodynamic preference for the BB-product over the AB-product was observed.

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Authors and Affiliations

  1.  Institut für Organische Chemie der Technischen Universität Wien, A-1060 Wien, Österreich

    Max Knollmüller, Peter Gärtner & Larissa Gaischin

  2.  Institut für Pharmazeutische Chemie der Johann Wolfgang Goethe – Universität, D-60439 Frankfurt am Main, Deutschland, DE

    Mathias Ferencic, Ulrich Girreser, Michael Klinge & Christian R. Noe

  3.  Institut für Mineralogie, Kristallographie und Strukturchemie der Technischen Universität Wien, A-1060 Wien, Österreich, Österreich

    Kurt Mereiter

Authors
  1. Max Knollmüller
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  2. Mathias Ferencic
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  3. Peter Gärtner
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  4. Ulrich Girreser
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  5. Michael Klinge
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  6. Larissa Gaischin
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  7. Kurt Mereiter
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  8. Christian R. Noe
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Additional information

Received November 12, 1998. Accepted (revised) December 9, 1998

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Knollmüller, M., Ferencic, M., Gärtner, P. et al. Addition von enantiomerenreinen Aminen an aktivierte Olefine, 2. Mitt. Über die Addition an (E)-4-Oxo-4-phenyl-2-butensäure-ethylester. Monatshefte fuer Chemie 130, 769–782 (1999). https://doi.org/10.1007/PL00010259

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  • DOI: https://doi.org/10.1007/PL00010259

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