Asymmetric synthesis of fluorine- and phosphorus-containing analogues of aminoacids

Nonracemic menthyl phosphorylacetates

“…The reaction of diethyl menthyl phosphite (1) or di O,O menthyl phenylphosphonite (2) with menthyl chloroacetate (Scheme 1) proceeds under more drastic conditions than the reaction with methyl chloroacetate, requires the presence of catalytic amounts of zinc chlo ride, and is accompanied by elimination of chloroethane, while the menthoxy substituent remains intact. The pres ence of the latter in products 3-5 was confirmed by mass spectrometry and 1 H NMR spectroscopy.…”

Synthesis of new functionalized organophosphorus acids and their derivatives with indan‐1‐carboxylic acid moieties

“…These compounds, including a hydrolytically stable P‐C bond, effectively interact with various enzymes and have a variety of biological activities. Unusual organophosphorus analogs of important amino acids (for example, phenylalanine, tyrosine, tryptophan), including aromatic, heterocyclic, and bicyclic groups, are of particular interest . Recently, we obtained mono‐ and diphosphorus‐substituted proline derivatives, as well as derivatives of mono‐ and diphosphonic acids, including moieties of five‐membered azaheterocycles[7a] with P‐C‐N systems, using trimethylsilyl esters of trivalent phosphorus acid.…”

Synthesis of new mono‐ and bisorganophosphorus proline derivatives with P–C–N moieties

“…Many of these substances including nonhydrolysable P-C bonds interfere with various enzymatic processes and possess the antibacterial, antiviral, antibiotic, pesticidal, antitumor, and enzyme inhibitory properties. [1][2][3][4][5][6][7][8][9] Several phosphorus containing peptides with proline moieties have attached attention in the capacity of the competitive inhibitors of human immunodeficiency virus protease. [10,11] Recently, the organophosphorus derivatives of glycine, β-alanine, and γ-aminobutyric acid with PCH 2 N moieties have been synthesized by us using various hexahydrotriazines.…”