26515-05-9

Upstream product

• 159405-40-0 (Ethyl-phenyl-phosphinoyl)-acetic acid methyl ester 
• 70795-79-8 R(-)-Ethylphenyl-phosphinigsaere-diethylamid 
• 35376-32-0 S⁽¹⁺⁾-Benzyl-ethyl-methyl-phenyl-phosphoniumiodid 
• 70795-79-8 ethyl-phenyl-phosphinous acid diethylamide 
• 15849-84-0 (+)-(S)-methylethylphenylphosphine 
• 159303-57-8 ((S)-Phenyl-vinyl-phosphinoyl)-acetic acid methyl ester 
• 159303-56-7 ((R)-Ethyl-phenyl-phosphinoyl)-acetic acid methyl ester 
• 77085-90-6 (-)-(R_P)-ethyl((menthoxycarbonyl)methyl)phenylphosphine oxide 
• 124081-58-9 (-)-R-(1-bromovinyl)methylphenylphosphine oxide 
• 89438-78-8 (-)-(S_P)-methylphenylvinylphosphine oxide 
• 917-64-6 methyl magnesium iodide 
• 87219-87-2 (R)-Ethyl-phenyl-phosphinic acid (S)-3-iodo-1-methyl-propyl ester 
• 7309-49-1 ethylmethylphenylphosphine oxide 
• 7301-81-7 ethyl (S)-methyl(phenyl)phosphinate 

Relevant academic research and scientific papers

A facile and practical preparation ofP-chiral phosphine oxides

A practical and cost-effective synthetic method ofP-chiral diarylalkyl, aryldialkyl, and triaryl phosphine oxides by using readily available chiral diphenyl-2-pyrrolidinemethanol as the auxiliary is developed. The long-standing racemization issue during s

Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery

Several dialkyl-arylphosphine oxides were prepared, and the enantioseparation of the corresponding racemates was elaborated with host–guest complexation using TADDOL-derivatives. The crystallization conditions were optimized and two separate crystallization methods, one in organic solvent, and the other in water, were found to yield five examples of phosphine oxides with enantiomeric excess values higher than 94 %. A gram scale resolution was performed, and both enantiomers of the methyl-phenyl-propyl-phosphine oxide were separated with (R,R)- or (S,S)-spiro-TADDOL. The intermolecular interactions responsible for the enantiomeric recognition between the chiral host and guest molecules were investigated by single-crystal X-ray diffractional structural determinations. The similarities in the structural patterns of a few diastereomeric crystals were checked by powder X-ray diffraction, as well. Organic solvent nanofiltration (OSN) was used as a scalable technique for the decomposition of the corresponding phosphine oxide–spiro-TADDOL molecular complexes, and for the recovery of the phosphine oxide enantiomers and resolving agents.

Stereoselective catalytic synthesis of P-stereogenic oxides via hydrogenative kinetic resolution

A highly stereoselective catalytic method for the preparation of structurally diverse P-stereogenic oxides has been developed. The approach relies on the ability of rhodium complexes derived from an enantiopure P-OP ligand to kinetically resolve racemic α,β-unsaturated phosphane oxides by hydrogenation of the C= C motif and formation of highly enantioenriched (or even enantiopure) P-stereogenic oxides. The practicality of the methodology has been demonstrated by the preparation of potentially functional P-chiral molecules for catalytic enantioselective synthesis.

First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane

P-Hydroxytetraorganophosphorane, the long-postulated intermediate in phosphonium salt and ylide hydrolysis, has been observed and characterised by low temperature NMR, finally definitively establishing its involvement in these reactions. The results require modification of the previously accepted mechanism for ylide hydrolysis: P-hydroxytetraorganophosphorane is generated directly by 4-centre reaction of ylide with water. This journal is

D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides

D-Glucosamine was successfully employed as a chiral auxiliary for the enantioselective synthesis of phosphine oxides. The influence of the anomeric position was also investigated and revealed the excellent ability of the α-anomer to perform this transform

Experimental and theoretical investigations of the stereoselective synthesis of P-stereogenic phosphine oxides

An efficient enantioselective strategy for the synthesis of variously substituted phosphine oxides has been developed, incorporating the use of (1S,2S)-2-aminocyclohexanol as the chiral auxiliary. The method relies on three key steps: 1) Highly diastereoselective formation of PV oxazaphospholidine, rationalized by a theoretical study; 2) highly diastereoselective ring-opening of the oxazaphospholidine oxide with organometallic reagents that takes place with inversion of configuration at the P atom; 3) enantioselective synthesis of phosphine oxides by cleavage of the remaining P-O bond. Interestingly, the use of a PIII phosphine precursor afforded a P-epimer oxazaphospholidine. Hence, the two enantiomeric phosphine oxides can be synthesized starting from either a PV or a PIII phosphine precursor, which constitutes a clear advantage for the stereoselective synthesis of sterically hindered phosphine oxides. That's handy: An efficient enantioselective strategy for the synthesis of variously substituted phosphine oxides was developed, incorporating the use of (1S,2S)-2-aminocyclohexanol as a chiral auxiliary, whereby enantiomeric phosphine oxides can be synthesized starting from either a PV or a PIII phosphine precursor.

Synthesis of P-chiral, non-racemic phosphinylacetates via enzymatic resolution of racemates

A series of racemic methyl phosphinylacetates was hydrolyzed in the presence of porcine liver esterase (PLE) under the kinetic resolution conditions to give the corresponding P-chiral phosphinylacetic acids and recovered esters in high enantiomeric purity (72-100% ee). The Jones' active site model was applied to explain the enantioselectivity of this reaction.

Enzymatic Resolution of Racemic Phosphinoylacetates Having a Stereogenic Phosphorus Atom

A series of racemic methyl alkylphenylphosphinoylacetates was hydrolyzed in the presence of pig liver esterase (PLE) to give the corresponding P-chiral phosphinoylacetic acids and unreacted esters in a high enantiomeric purity (72-100percent ee).

OPTICALLY ACTIVE PHOSPHINE OXIDES. 8. SYNTHESIS OF NONSYMMETRICAL 1,2-DIPHOSPHINYLETHENES AND RELATED SYSTEMS

The synthesis of the nonsymmetrical and the optically active trans-1,2-diphosphinylethenes has been accomplished.The employed addition-elimination route is potentially general and utilizes readily accessible secondary phosphine oxides and tertiary 1-halog

Optically Active Phosphine Oxides. 2. Novel Approach to Enantiomeric Dialkylphenylphosphine Oxides

New routes to optically active tertiary phosphine oxides of known configuration and of virtually 100percent enantiomeric purity have been developed.Alkylation of (-)-(SP)-ethyl((menthoxycarbonyl)methyl)phenylphosphine oxide (2) by treatment wit