A convenient synthesis of perfluoroalkylated enamines and vinyl phosphonates

Synthesis of perfluoroalkylated?-alanine and some peptide derivatives: An access to original surfactants

“…Cen reported on a synthesis of fluorinated enamines by reacting fluoroalkynes with amines or ammonia in alcoholic solution (Cen et al, 1995). The fluorine-containing enamines were hydrogenated to yield the precursor of fluoroalkyl-fi-alanine (Scheme 3).…”

“…Synthesis of perfluoroalkylated fi-aminoacids from fluoroalkynes (Cen, 1995) 1) NaOH, 2N, THF Synthesis of perfluoroalkylated fi-aminoacids from fluoroalkynes (Cen, 1995) 1) NaOH, 2N, THF…”

A Cascade Approach to Captodative Trifluoromethylated Enamines or Vinylogous Guanidinium Salts: Aromatic Substituents as Switches of Reaction Direction

“…Generally, the position of the nitro substituent in the aryl group or the nature of the vinylic halogen atom (Br or Cl) in the initial substrate 1, as well as the steric and electronic effects of the substituent on the nitrogen atom of the aliphatic amine, have just a small influence on the yields and stereoselectivities. The best results were achieved when basic primary amines were used as nucleophiles ( Table 1, Entries [1][2][3][4][5][6][7][8][9][10][11][12]. It should be noted that decreased nucleophilicity resulted in reaction failure with aromatic amines ( Table 1, Entries 13, 14).…”

“…It is no surprise that different efforts to prepare α-polyfluoroalkyl-containing enamines have been undertaken, including Wittig reactions with trifluoroacetamides, [3,4] treatment of amines with perfluoroalkyl ketones, [5] additions of amines to trifluoromethylacetylenes [6] and direct trifluoromethylation of pyrrolidinones. [7] A simple method for the preparation of fluoroalkyl β-enaminophosphonates from alkylphosphonates and perfluoroalkyl nitriles has also been reported.…”

Stereoselective synthesis of trifluoromethylated vinyl- and dienylphosphonates with γ-alkoxycarbonyl moiety

“…Organofluorine compounds are increasingly being applied in pharmaceuticals, agrochemicals and other fields [6][7][8] since the introduction of fluorine or trifluoromethyl group into biologically active compounds often gives rise to unique physiological activities [9,10]. However, the methodology for the synthesis of fluorinated vinylphosphonates is still limited [11][12][13][14][15].…”