184535-63-5

Upstream product

• 3220-50-6 1-phenylvinylphosphonic acid 
• 98-86-2 acetophenone 
• 172878-13-6 (S)-(2l,6l,1'u)-6-methyl-3-(1-methylethyl)-2-(1'-phenylethyl)-1,3,2-oxazaphosphorinane 2-sulfide 
• 172878-06-7 (S)-(2l,6l)-6-methyl-3-(1-methylethyl)-2-(phenylmethyl)-1,3,2-oxazaphosphorinane 2-sulfide 
• 145124-62-5 (S)-(2u,6l)-6-methyl-3-(1-methylethyl)-2-(phenylmethyl)-1,3,2-oxazaphosphorinane 2-oxide 
• 1499-19-0 benzylphosphonic dichloride 
• 156406-83-6 (S)-(2u,6l,1'u)-3-(1-methylethyl)-2-(1'-phenylethyl)-6-methyl-1,3,2-oxazaphosphorinane 2-oxide 

Downstream Products

• 130696-25-2 (1R)-(+)-1-phenethyl dimethylphosphonate 

Relevant academic research and scientific papers

Rh/SPO-WudaPhos-Catalyzed Asymmetric Hydrogenation of α-Substituted Ethenylphosphonic Acids via Noncovalent Ion-Pair Interaction

Asymmetric hydrogenation of α-substituted ethenylphosphonic acids has been successfully achieved by Rh/ferrocenyl chiral bisphosphorus ligand (SPO-Wudaphos) through noncovalent ion-pair interaction between the substrate and catalyst under mild reaction co

Rh(I)-catalyzed enantioselective hydrogenation of α-substituted ethenylphosphonic acids

A class of chiral Rh(I) catalysts containing monodentate phosphorous acid diesters tautomerized from the corresponding secondary phosphine oxides was discovered by serendipitous hydrolysis of phosphoramidite ligands. The evolved catalysts demonstrated unprecedented enantioselectivities (98-99% ee) and high catalytic activities (as low as 0.01 mol% catalyst loading) in asymmetric hydrogenations of a wide variety of α-aryl-/alkyl-substituted ethenylphosphonic acids, providing a facile approach to the corresponding enantiopure phosphonic acids with significant biological importance.

Impact on hydrogenation catalytic cycle of the R groups Cyclic feature in "r-SMS-Phos"

A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ees also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.

Synthesis of biologically active 1-arylethylphosphonates

A convenient and inexpensive general preparation method for 1-arylethylphosphonic acids and their esters was developed involving in reduction of the corresponding 1-ethenylphosphonates by ammonium formate in the presence of palladium on carbon. A homogeneous enantioselective hydrogenation of 1-arylethenylphosphonic acids in the presence of chiral ruthenium catalysts provided optically active 1-arylethylphosphonic acids of enantiomeric purity up to 86%. The preliminary data on biological activity testing of the 1-arylethylphosphoic acids synthesized evidence that some among the compounds obtained are low-toxic substances with the properties of immunosuppressors of the central type of action.

A practical synthetic approach to chiral α-aryl substituted ethylphosphonates

A convenient general method is reported for the synthesis of α-aryl substituted ethylphosphonic acids and esters by hydrogenation of α-aryl substituted ethenylphosphonic acids and esters. Racemic α-arylethylphosphonic acids and esters were prepared in 70-88% yield under palladium-assisted transfer hydrogenation conditions using ammonium formate. Asymmetric hydrogenation of α-arylethenylphosphonic acids using chiral Ru(II) catalysts led to α-arylethylphosphonic acids with enantiomeric excesses up to 86%.

Asymmetric hydrogenation of vinylphosphonic acids and esters with chiral Ru(II) catalysts

The first asymmetric hydrogenation of vinylphosphonic acids and esters to the corresponding arylethylphosphonic acids and esters using chiral Ru(II) catalysts is reported with enantiomeric excesses up to 86%.

The asymmetric synthesis of α-substituted α-methyl and α-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides

The design, preparation, structural and spectroscopic analyses of topologically unique and enantiomerically pure alkyl phosphonamides are described. In the case of α-ethyl and α-benzyl phosphonamides, the geometry of both the secondary and tertiary carbanions was determined to be planar through deprotonation/deuteration/alkylation experiments. Stereoselective alkylations of such systems proceeded in good yields and with high diastereoselectivities. The resulting α,α-alkylated phosphonamides were hydrolyzed to give the corresponding α,α-alkyl phosphonic acids with high degrees of enantiomeric purity.

Alkylations of chiral, phosphoryl- and thiophosphoryl-stabilized carbanions

A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different α-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidat