Efficient synthesis of 3-furanosyl-6'-furanosylphosphinate through a tandem sequential radical process.
The sodium salt of hypophosphorous acid is shown to act as a double radical precursor in a double, sequential radical addition on 3-exo-methylenefuranose derivative 14 and 4-ethylenefuranose 10 to furnish phosphinates 18d in good overall yields. Unambiguous structural assignment establishes the high diastereoselection of the process.
Dubert
Olivier
O
Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014 CNRS, Université de Rouen, IRCOF, Rue Tesnière, F-76821 Mont Saint Aignan, France.
Gautier
Arnaud
A
Condamine
Eric
E
Piettre
Serge R
SR