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Synthesis 1990; 1990(2): 132-134
DOI: 10.1055/s-1990-26810
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Phosphoranaloge von Aminosäuren III1. Synthese optisch aktiver 1-Aminoalkylphosphonsäuren der (S)- und (R)-Reihe mit Hilfe von (-)-Ephedrin als Auxiliar

Michael Sting* , Wolfgang Steglich
  • *Institut für Organische Chemie and Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-5300 Bonn 1, Federal Republic of Germany
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Publikationsdatum:
17. September 2002 (online)

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Synthesis of Optically Active (S)- and (R)-1-Aminoalkylphosphonic Acids Using (-)-Ephedrine as Auxiliary The 2-benzoylaminomethyl-3,4-dimethyl-2-oxo-5-phenyl-2λ5-1, 3,2-oxazaphospholidines 2 and 2′, epimeric at the 2-position, are easily obtainable from benzoylaminomethylphosphonic acid dichloride (1) and (-)-ephedrine and are diastereoselectively alkylated at the P-C-N methylene group to yield compounds 3 and 3′, respectively. Hydrolysis of these products affords 1-aminoalkylphosphonic acids 4 and 4′, with (S)- and (R)-configuration, respectively.