Synthesis 2020; 52(16): 2364-2372
DOI: 10.1055/s-0040-1707813
paper
© Georg Thieme Verlag Stuttgart · New York

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

a  Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland
b  Centre for Advanced Technologies, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 10, 61-614 Poznań, Poland   Email: marcin.kazmierczak@amu.edu.pl
,
a  Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland
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a  Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland
› Author Affiliations
M. K. would like to thank the National Science Centre (Narodowe Centrum­ Nauki) for partial financial support under grant 2018/02/X/ST5/02867 (MINIATURA 2).
Further Information

Publication History

Received: 16 March 2020

Accepted after revision: 15 April 2020

Publication Date:
13 May 2020 (online)


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

Supporting Information

 
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