Application of α-Amino-β-fluorophosphonates in Construction of their Dipeptide Analogues

Marcin Kaźmierczak; Grzegorz Dutkiewicz; Tomasz Cytlak

doi:10.1055/s-0040-1707813

Synthesis, Table of Contents

Synthesis 2020; 52(16): 2364-2372
DOI: 10.1055/s-0040-1707813

paper

Application of α-Amino-β-fluorophosphonates in Construction of their Dipeptide Analogues

Marcin Kaźmierczak ∗

^aFaculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland

^bCentre for Advanced Technologies, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 10, 61-614 Poznań, Poland Email: marcin.kazmierczak@amu.edu.pl

,

Grzegorz Dutkiewicz

^aFaculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland

,

Tomasz Cytlak

^aFaculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland

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Abstract

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Dedication to Professor Henryk Koroniak in honor of his 70^th birthday.

Abstract

Herein, we present application of α-amino-β-fluorophosphonates for the construction of their dipeptide analogues. α-Amino-β-fluorophosphonates were prepared in a XtalFluor-E mediated deoxyfluorination of α-hydroxy-β-aminophosphonates. The reaction proceeds through an aziridinium ion formation, which was confirmed by the formation of a hexacoordinate phosphorus compound. Moreover, the absolute configuration of the obtained compounds was determined by X-ray analysis, which proved the stereochemistry.

Key words

fluorinated aminophosphonates - nucleophilic fluorination - fluorine - phosphorus - dipeptide analogues

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References

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