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Synthesis 2020; 52(16): 2364-2372
DOI: 10.1055/s-0040-1707813
DOI: 10.1055/s-0040-1707813
paper
Application of α-Amino-β-fluorophosphonates in Construction of their Dipeptide Analogues
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.
Key words
fluorinated aminophosphonates - nucleophilic fluorination - fluorine - phosphorus - dipeptide analoguesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707813.
- Supporting Information
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