721-74-4

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 16934-92-2 (R_p)-menthyl methylphenylphosphinate 
• 111-25-1 1-bromo-hexane 
• 100-39-0 benzyl bromide 
• 16934-93-3 (S_p)-Menthylmethylphenylphosphinate 
• 126441-54-1 R_p-(-)-menthyl benzylmethylphosphinate 
• 23275-37-8 (+)-(R)-benzyl-methyl-phenylphosphine 
• 917-54-4 methyllithium 
• 184776-16-7 (D)-1,2:5,6-diisopropylidene-α-D-glucofuranosyl benzylphenylphosphinate 
• 75-16-1 methylmagnesium bromide 
• 4545-85-1 benzyldichlorophosphane 
• 87214-10-6 C₂₃H₂₅BrNOP 
• 2746-25-0 p-Methoxybenzyl bromide 
• 87214-12-8 (S)-Benzyl-phenyl-phosphinic acid methyl ester 

Downstream Products

• 5137-89-3 S(+)-Benzyl-methyl-phenyl-n-propyl-phosphoniumbromid 
• 23275-37-8 (+)-(R)-benzyl-methyl-phenylphosphine 

Relevant academic research and scientific papers

Ni-Catalyzed Enantioselective Benzylation of Secondary Phosphine Oxide

A nickel-catalyzed benzylic substitution of secondary phosphine oxide was described, affording the dialkylated P-stereogenic tertiary phosphine oxides with high to excellent enantioselectivities. The reaction was performed under mild conditions with commercially available benzyl chlorides and bench stable secondary phosphine oxides, exhibiting broad functional group tolerance. It represented a practical example for the preparation of P-stereogenic phosphine compounds.

Cobalt-Catalysed Asymmetric Addition and Alkylation of Secondary Phosphine Oxides for the Synthesis of P-Stereogenic Compounds

The catalytic asymmetric synthesis of P-chiral phosphorus compounds is an important way to construct P-chiral ligands. Herein, we report a new strategy that adopts the pyridinyl moiety as the coordinating group in the cobalt-catalysed asymmetric nucleophilic addition/alkylation of secondary phosphine oxides. A series of tertiary phosphine oxides were generated with up to 99 % yield and 99.5 % ee, and with broad functional-group tolerance. Mechanistic studies reveal that (R)-secondary phosphine oxides preferentially interact with the cobalt catalysts to produce P-stereogenic compounds.

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.

Simple route to chiral organophosphorus compounds

Reaction of chlorides of nonsymmetrically substituted phosphinic and phosphinous acid with (-)-1,2,3,5-disubstituted-α-D-glucofuranose proceeds with very high stereoselectivity to give stereochemically pure phosphinic and phosphinous acid esters, which are starting reagents for preparation of chiral organophosphorus compounds. Stereoselectivity of the reaction depends on the nature of bases, solvent, temperatures and excess of chlorophosphine.

STEREOSPECIFIC REDUCTION OF DIASTEREOMERICALLY PURE MENTHYL PHOSPHINATES: A NEW ROUTE TO OPTICALLY ACTIVE PHOSPHINE OXIDES

Diastereomerically pure menthyl phosphinates are stereospecifically reduced by lithium 4,4'-di-tert-butylbiphenylide.Subsequent treatment with alkyl halides affords phosphine oxides with high optical purity.

Asymmetric synthesis of phosphinates, phosphine oxides and phosphines by Michaelis Arbuzov rearrangement of chiral oxazaphospholidine

A general approach to asymmetric synthesis of high optically active tertiary organophosphorus compounds is described.Oxazaphospholidine 3 reacts with alkyl halide to give regio and stereoselectively the corresponding phosphinamide 4.Methyl phenyl phosphin

SYNTHESIS AND ABSOLUTE CONFIGURATION OF DIASTEREOMERIC MENTHYL BENZYLPHOSPHINATES

Diastereomerically pure Rp-menthyl benzylphosphinate (7a) and diastereomerically enriched Sp-menthyl benzylphosphinate (7b) have been prepared and their absolute configurations have been corroborated via chemical correlation.Key words: Phosphinic acid; chiral esters, absolute configuration; thermal epimerization; alkylation; reaction with Grignard reagent; chiral phosphine oxides.

PREPARATION OF OPTICALLY ACTIVE PHOSPHINE OXIDES BY REGIOSELECTIVE CLEAVAGE OF CYCLIC PHENYLPHOSPHONITE WITH ALKYL HALIDES

The Arbuzov reaction of (2S,4S)-methyl-2-phenyl-1,3,2-dioxaphosphorinane with various alkyl halides gave the diastereomerically pure phosphinates with regioselective cleavage of the primary carbon-oxygen bond.These phosphinates reacted with Grignard reage