Synthesis methods of (1-aminocyclopropyl)phosphonic acids

Exploiting Palladium-Catalyzed Cross-Coupling for the Synthesis of 2-Aryl-Substituted 1-Aminocyclopropylphosphonates

“…Although we did not experience any problems in handling (4-bromophenyl)-and [4-(diethoxyphosphoryl)phenyl]diazomethanes, full safety precautions should be taken due to their potential explosive nature). 1 H, 13 C, and 31 P NMR spectra were recorded on Bruker Avance-300, 400, or 500 instruments. 13 C and 31 P spectra were 1 H decoupled.…”

“…8 Synthetic approaches to this class of compounds reported so far are not numerous, and their scope and limitations have not been examined in detail. 1,9 Therefore further investigations in this field are highly desirable. Recently we have shown that 2-substituted 1-aminocyclopropylphosphonic acids can be prepared via regioselective 1,3-dipolar cycloaddition reaction of diazo compounds with dimethyl 1-formamidovinylphosphonate (1) followed by thermal deazetization of the formed 1-pyrazolines 2 (Scheme 1).…”

“…1,9 Therefore further investigations in this field are highly desirable. Recently we have shown that 2-substituted 1-aminocyclopropylphosphonic acids can be prepared via regioselective 1,3-dipolar cycloaddition reaction of diazo compounds with dimethyl 1-formamidovinylphosphonate (1) followed by thermal deazetization of the formed 1-pyrazolines 2 (Scheme 1). 10 Scheme 1 Diazo addition method for the synthesis of 2-substituted 1-aminocyclopropylphosphonic acids In continuation of this work we attempted to extend the method to the synthesis of substituted 1-aminocyclopropylphosphonates containing an additional remote phosphonate fragment, applicable for grafting onto an inorganic matrix when designing functional surfaces in the biomaterials area.…”

“…1 It mimics 1-aminocyclopropanecarboxylic acid, exhibits a potent inhibitor activity towards pyridoxal 5′-phosphate dependent enzymes, 2 and has been used in probing the active site of 1-aminocyclopropane-1-carboxylate deaminase and the enzymatic reaction mechanism. 3 2-Substituted 1-aminocyclopropylphosphonic acids have been designed as phosphorus analogues of (-)-allonorcoronamic acid 4 and (-)-(Z)-2,3-methanohomoserine, 5 they are also structural moieties of oligopeptides that are promising in the treatment of hepatitis C virus infection.…”

Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives

“…These classes of compounds are currently attracting great interest in organic and medicinal chemistry, as well as in agriculture, due to their important biological and pharmacological properties [1][2][3][4][5]. The great importance of this type of compounds has prompted organic chemists to report numerous procedures for their racemic or stereoselective synthesis [6][7][8][9][10][11]. On the other hand, the optically active α-amino-C-phosphinic acids 3 are also considered as analogues of α-amino acids 2 where now the carboxylic group (CO 2 H) is replaced by a tetrahedral and sterically more demanding phosphinic acid functionality (PO 2 HR ).…”