Catalytic Reactions in Fluorinated Phosphonates Synthesis

Transformations of a-hydroxyphosphonates derived from proline or serine by treatment with different deoxyfluorinating reagents (DAST, Deoxofluor, PyFluor) are reported. Depending on the applied reagent, as well as the protecting group used (N-Cbz, N-Boc, N-Bn) different types of products are observed. The reaction of N-Cbz or N-Boc prolinols with DAST or Deoxofluor due to aziridinium intermediate participation gave fluorinated amino phosphonates such as piperidine and pyrrolidine derivatives and/or oxazolidine-2-ones. Similarly, the analogous reaction of N-Cbz or N-Boc protected serinol yielded oxazolidine-2-ones or its fluorinated analogues. As the second type of product formed by DASTinduced reaction of serine derivatives, aziridines were obtained. Only in the case of deoxyfluorination of N-benzyl prolinols were both diastereoisomers of b-fluoropiperidine-a-phosphonates formed, while the reaction of protected N-benzyl serinols gave fluorinated oxazolidines. Moreover, application of PyFluor gave sulfonate derivatives.

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Latest achievements in the preparation of fluorinated aminophosphonates and aminophosphonic acids

Cytlak

Kaźmierczak

Skibińska

et al. 2017

Phosphorus, Sulfur, and Silicon and the Related Elements

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Catalytic Reactions in Fluorinated Phosphonates Synthesis

Abstract: The goal of this review is to describe recent advances in metal catalyzed reactions and organocatalysis leading to-monofluoro- , ,-gem-difluoro-or trifluoromethyl phosphonate derivatives with a particular emphasis on introducing chiral centers in these compounds.

Cited by 3 publications

References 48 publications

Condensation of diethyl fluoromethylphosphonate with esters: An alternative synthetic route to diethyl α-fluoro-β-ketophosphonates

Condensation of diethyl fluoromethylphosphonate with esters: An alternative synthetic route to diethyl α-fluoro-β-ketophosphonates

Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of α-hydroxyphosphonates induced by deoxyfluorinating reagents

Latest achievements in the preparation of fluorinated aminophosphonates and aminophosphonic acids

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