83567-77-5Relevant articles and documents
α,α-Difluoro-β-iminophosphonates, an alternative strategy towards the synthesis of α,α-difluoro-β-aminophosphonate derivatives
Szewczyk,Rapp,Virieux,Pirat,Koroniak
supporting information, p. 6322 - 6333 (2017/07/17)
α,α-Difluoromethylenephosphonates are generally known as stable natural phosphate mimics with significantly improved biological activities. A number of α,α-difluoroalkylphosphonates have already been found to be important enzyme inhibitors. Herein, we report an alternative strategy towards the synthesis of α,α-difluoromethylene-β-aminophosphonate derivatives. A small library of N-substituted α,α-difluoro-β-aminophosphonates was designed and described via NMR study. The protocol began with the condensation of β-ketophosphonates with a series of primary amines. The key step of the synthesis is an electrophilic fluorination, mediated by Selectfluor, of the mixture of β-enamino/β-iminophosphonates leading to α,α-difluoro-β-iminophosphonates followed by reduction. The title compounds may behave as convenient building blocks for further more advanced modification.
Reformatsky-type co-mediated synthesis of β-hydroxyphosphonates
Orsini, Fulvia
, p. 1425 - 1428 (2007/10/03)
Low-valent cobalt complexes were used in Reformatsky-type additions of α-halophosphonates to carbonyl compounds (ketones and aldehydes) to yield a variety of β-hydroxyphosphonates.
AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF 1,1-DIFLUORO-2-HYDROXYALKYLPHOSPHONATES
Obayashi, Michio,Kondo, Kiyosi
, p. 2327 - 2328 (2007/10/02)
The reaction of diethyl difluoro(trimethylsilyl)methylphosphonate with arenecarbaldehydes and aryl methyl ketones is effected with the aid of a catalyst, cesium fluoride, at room temperature to afford the title compounds.
