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

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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