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Synthesis 1992; 1992(5): 487-490
DOI: 10.1055/s-1992-26143
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Diastereoselective Formation of (Z)-Didehydroamino Acid Esters

Ulrich Schmidt* , Helmut Griesser, Volker Leitenberger, Albrecht Lieberknecht, Rainer Mangold, Regina Meyer, Bernd Riedl
  • *Institut für Organische Chemie und Isotopenforschung der Universität Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, Germany
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Publication Date:
17 September 2002 (online)

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The rearrangement of (E)-didehydroamino acid derivatives to the corresponding Z-derivatives under acid or basic catalysis as well as under the influence of radicals has been investigated. The condensation of N-benzyloxycarbonyl or N-tert-butoxycarbonyl protected alkyl 2-amino-2-(dimethoxyphosphoryl)acetates with aldehydes or ketones in dichloromethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene furnishes (Z)-didehydroamino acid ester derivatives diastereoselectively in excellent yields and with high purity.