Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids

Groth, Ulrich; Lehmann, Lutz; Richter, Lutz; Schöllkopf, Ulrich

Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids

Dateien

Synthesis_of_Diastereomerically_Pure_1_Aminocyclopropylphosphonic_Acids.pdfGröße: 624.29 KBDownloads: 353

Datum

1993

Autor:innen

Groth, Ulrich

Lehmann, Lutz

Richter, Lutz

Schöllkopf, Ulrich

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

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.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

Alpha-Aminophosphonic acids, Cyclopropanation, diastereoselective, Isocyanides

Zitieren

ISO 690

GROTH, 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}
}

RDF

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Universitätsbibliographie

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