New synthesis of fluorinated 2-aminophosphonates

Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides

“…We then examined the effect of the phosphonate ester groups on the diastereoselectivity of addition to imine (S)-1. In general, various phosphonates 2a,c,d participated successfully in the reaction under optimised reaction conditions providing the corresponding addition products (Ss,R)-4a,c,d in moderate to good yields and excellent diastereoselectivities (Table 1, entries [6][7][8]. The use of the least hindered dimethyl methylphosphonate 2a gave addition product with diastereoisomeric ratio similar to that found for the diisopropyl methylphosphonate 2d albeit in lower yield.…”

“…6 The most general approach to racemic fluoroalkylated b-aminophosphonates consists of reduction of b-enaminophosphonates containing fluoroalkyl substituents at the b position. 7 Other methods for the synthesis of racemic fluoroalkylated b-aminophosphonates are limited to some procedures developed for addition of amines or ammonia to a,b-unsaturated phosphonates, 8 ring opening of trifluoromethyl aziridine-2-phosphonates 9 and addition of carbanions generated from phosphonates to trifluoromethyl N-benzoyl and N-carbalkoxy imines. 10 To the best of our knowledge, there is only one report in the literature dealing with preparation of optically enriched fluoroalkylated b-aminophosphonates.…”

Synthesis and Characterization of Novel Azo Disperse Dyes Containing -amino Phosphonate and Their Dyeing Performance on Polyester Fabric

“…Among α-functional phosphonic acids, α-aminophosphonic acids, and α-amino phosphonate are supreme important compounds which provides a diversity of important and preferable properties. A considerable number of α-amino phosphonate derivatives are known to be bioactive, they display an antiviral, antibacterial, antifungal, antimicrobial and antitumor activity [7][8][9][10][11][12][13][14][15][16].…”

Synthesis and bioactivity of fluorine compounds containing isoxazolylamino and phosphonate groups

“…A considerable number of a-aminophosphonate derivatives are known to be bioactive. They display antiviral, antibacterial, antifungal, antimicrobial, and antitumor activities [1][2][3][4][5][6][7][8][9][10]. In our previous work, through modifying its structure by replacement of phenylamino substituent with 4-trifluoromethylphenylamino group, we found that some of them showed excellent virucidal activities [11][12][13][14].…”