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Synthesis 1995; 1995(1): 44-46
DOI: 10.1055/s-1995-3843
short paper
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Aziridines; 65. Acyclic and Cyclic γ-Amidopropanephosphonic Esters by Amidoethylation of Horner Reagents with Activated Aziridines

T. Baumann, B. Buchholz, H. Stamm*
  • *Pharmazeutisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 364, D-69120 Heidelberg, Germany
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Publication Date:
31 December 2000 (online)

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The carbanions of Horner reagents (α-cyanated and α-acylated phosphonic esters 2, 8 and 11) are amidoethylated with activated aziridines 1a-e. Twofold amidoethylation is observed with the phosphononitrile 2 only. The primary products 9 formed from the phosphono acetate 8 tend to cyclize yielding phosphonopyrrolidinones 10.

Horner reagents are amidomethylated with activated aziridines

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