Potential chemical transformation of phosphinic acid derivatives and their applications in the synthesis of drugs

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

“…The organophosphates encompass a major class of biomedically and industrially important materials. Thus, significant progress in the reactions that generate phosphorous-carbon bonds has been made [ 5 , 35 , 108 , 109 , 110 ]. Nevertheless, this rapid expansion in organophosphorus chemistry has called for the detailed review and discussion of the progress that has been made in certain named reactions that generate P–C bonds.…”

“…Here, a detailed presentation of the improvements and variations of the MA reaction is given, with potential applications in the biomedical field. Previous review articles have not dealt in detail with the MA reaction and its applications since 1985 [ 5 , 11 , 35 , 108 , 109 , 110 ].…”

“…BTSP is prepared by the reaction of hypophosphorous acid with silylating agent N,O-bis(trimethylsilyl)acetamide ( Scheme 23 ) [ 34 ]. A classic example of the silyl–Arbuzov reaction is the synthesis of lesogaberan, an investigative drug for the treatment of gastroesophageal reflux that is presented later in this review [ 35 ].…”

“…Lesogaberan is a drug under study for the treatment of gastroesophageal reflux. The synthesis of lesogaberan is shown in Scheme 59 and requires the modified MA reaction between (R)-2-fluoro-3-iodopropylamine and BTSP that was described previously [ 35 ].…”

Access to α-Aminophosphonic Acid Derivatives and Phosphonopeptides by [Rh(P–OP)]-Catalyzed Stereoselective Hydrogenation

“…The preparation of enantioenriched α-aminophosphonic acid derivatives employing enantioselective catalytic methods is still a non-fully developed area of research. These compounds are highly important in the pharmaceutical and agrochemical sectors, as they are key building blocks for the synthesis of biologically active molecules such as P -containing peptides and related compounds. , The configuration at the P , N -disubstituted carbon is essential to trigger the desired biological activity in the final molecules. , Consequently, the development of asymmetric catalytic methodologies for the preparation of both enantiomers of such compounds would be highly desirable. From the different alternatives for their catalytic asymmetric synthesis, , enantioselective hydrogenation (AH) of suitable precursors should be considered an operationally simple and suitable strategy for their preparation .…”