Publikation: Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids
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1993
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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.
Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
540 Chemie
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Alpha-Aminophosphonic acids, Cyclopropanation, diastereoselective, Isocyanides
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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.199319930169BibTex
@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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<dcterms:abstract xml:lang="eng">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.</dcterms:abstract>
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