57483-33-7Relevant academic research and scientific papers
Chemoselective Reduction of the P=O Bond in the Presence of P–O and P–N Bonds in Phosphonate and Phosphinate Derivatives
Sowa, Sylwia,Pietrusiewicz, K. Micha?
supporting information, p. 923 - 938 (2019/01/22)
Chemoselective reduction of the strong P=O bond in the presence of weaker P–O (ester) and P–N (amide) bonds in phosphonic acid derivatives has constituted an unresolved problem in organophosphorus chemistry for years. This long-standing problem is now solved for biologically relevant α-hydroxy and α-amino phosphonic as well as phosphinic acids esters and amides. The reduction of the P=O bond without concomitant scission of the ester and amide bonds is affected by use of BH3, a mild reducing agent, which affords the corresponding borane protected PIII phosphonite and phosphinite derivatives in one step. A mechanistic rationale is proposed for the role played by neighboring OH and NHR groups in facilitating the reduction, and for the observed chemo- and stereoselectivity. The reduction methodology described opens previously unavailable synthetic options in chemistry of α-functionalized phosphonic and phosphinic acids by offering a unique possibility for direct modifications of oxidation level of the P-center in these compounds.
Lipase-catalysed resolution of 1-hydroxyethane-P-phenylphosphinates
Majewska,Kafarski,Lejczak
, p. 561 - 566 (2007/10/03)
Lipase-catalysed hydrolysis and transesterification were used to obtain α-hydroxyalkanephosphinates with two stereogenic centers, namely at α-carbon and phosphorus atoms. These compounds were chosen to check if there is a transfer of chirality from carbon
New syntheses of 1-chloroalkylphosphinates
Morise, Xavier,Savignac, Philippe,Denis, Jean-Marc
, p. 2179 - 2185 (2007/10/03)
Different approaches to the synthesis of 1-chloroalkylphosphinates are described. Initially, we tried to extend a reaction described by Kabachnik for the preparation of chloromethylphosphinic acid chlorides [R1(Cl)P(O)CH2Cl] to C-substituted derivatives. We also considered the possibility of synthesizing the title compounds by routes already described for the formation of diethyl 1-chloroalkylphosphonates. Although these methods have allowed us to obtain several of the desired phosphinates, they suffer from limitations that restrict their synthetic applications. Finally, we have developed a more general approach that allows the formation of a wide range of phosphinates. It involves a selective P-C bond formation by reaction of MeMgCl and PhMgCl with phosphonochloridates, which are prepared by P-chlorination of 1-chloroalkylphosphonates.
A CONVENIENT SYNTHESIS OF O-ETHYL-1-AMINOALKYLPHOSPHINATES
Gajda, Tadeusz
, p. 59 - 64 (2007/10/02)
1-Aminoalkylphosphinates 4 have been obtained in good yields in a one-step transformation by the Mitsunobu reaction of 1-hydroxyalkylphosphinates 1 with hydrazoic acid, and subsequent treatment of the intermediate azides 2, with triphenylphosphine, follow
