Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids

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1993
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Lehmann, Lutz
Richter, Lutz
Schöllkopf, Ulrich
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Liebigs Annalen der Chemie. 1993, 1993(4), pp. 427-431. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930169
Zusammenfassung

The lithium or potassium derivative of diethyl isocyanometh-ylphosphonate (1) reacts with epoxides in the presence of boron trifluoride-diethyl ether to provide the diethyl 3-hy-droxy-1-isocyanoalkylphosphonates rac-3. The corresponding mesylates rac-4 undergo a base-mediated cyclization to the diethyl 1-isocyanocyclopropylphosphonates rac-5. Acidic hydrolysis affords the diethyl l-aminocyanocyclopropylphos phonates roc-6, which upon treatment with trimethylsilyl iodide yield the 1-aminocyclopropylphosphonic acids rac-7. A base-mediated cycloalkylation of 1 with dibromoalkanes 10 gives the diethyl 1-isocyanocycloalkylphosphonates 11 which are suitable precursors for the achiral l-aminocycloal-kylphosphonic acids.

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540 Chemie
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Alpha-Aminophosphonic acids, Cyclopropanation, diastereoselective, Isocyanides
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ISO 690GROTH, Ulrich, Lutz LEHMANN, Lutz RICHTER, Ulrich SCHÖLLKOPF, 1993. Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids. In: Liebigs Annalen der Chemie. 1993, 1993(4), pp. 427-431. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930169
BibTex
@article{Groth1993Synth-9676,
  year={1993},
  doi={10.1002/jlac.199319930169},
  title={Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids},
  number={4},
  volume={1993},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={427--431},
  author={Groth, Ulrich and Lehmann, Lutz and Richter, Lutz and Schöllkopf, Ulrich}
}
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