Molecules (Sep 2019)

Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

  • Jakub Adamek,
  • Anna Węgrzyk-Schlieter,
  • Klaudia Steć,
  • Krzysztof Walczak,
  • Karol Erfurt

DOI
https://doi.org/10.3390/molecules24183405
Journal volume & issue
Vol. 24, no. 18
p. 3405

Abstract

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In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and N-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.

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