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Syntheses of α-Aminophosphonic Acids, VI. Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids

✍ Scribed by Groth, Ulrich ;Lehmann, Lutz ;Richter, Lutz ;Schöllkopfh, Ulrich

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
580 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The lithium or potassium derivative of diethyl isocyanomethylphosphonate (1) reacts with epoxides in the presence of boron trifluoride–diethyl ether to provide the diethyl 3‐hydroxy‐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 1‐aminocyanocyclopropylphosphonates rac‐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 1‐aminocycloalkylphosphonic acids.

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