757218-54-5

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 29949-69-7 tert-butylchlorophenylphosphane 
• 757218-54-5 (S(p))/(R(p))-tert-butyl(α-methylbenzylamino)phenylphosphine 

Downstream Products

• 6057-79-0 (S)-(-)-t-butyl(phenyl)phosphine oxide 
• 538311-41-0 (S_P,S)-N-(1-phenylethyl)amino-tert-butylphenylphosphine oxide 
• 757218-54-5 (R_P,S)-N-(1-methylbenzyl)amino-tert-butylphenylphosphine 

Relevant academic research and scientific papers

P-chirogenic diphosphazanes with axially chiral substituents and their use in rh-catalyzed asymmetric hydrogenation

A convenient synthesis of enantiopure P-chirogenic diphosphazanes incorporating bulky bisphenol and 1,1′-bi-2-naphtholderived substituents via the functionalization of a readily accessible enantiopure lithium phosphinoamide with chlorophosphoridites was developed. Since the product requires no subsequent deprotection, the protocol provides an easy, convenient synthesis of P-chirogenic ligands on the gram scale. The ligands were applied in the Rh-catalyzed asymmetric hydrogenation of benchmark substrates furnishing enantiomeric excess values up to 96%.

A practical method for N-alkylation of phosphinic (thio)amides with alcohols via transfer hydrogenation

This manuscript describes a modular method for preparing N-alkyl phosphinic amides from primary or secondary alcohols and primary phosphinic amide (R1R2P = ONH2) nucleophiles via transfer hydrogenation. The transformation typically proceeds in excellent yields, employs conveniently available reagents, and produces water as the only byproduct.

Stereochemistry of electrophilic and nucleophilic substitution at phosphorus

Stereochemistry and mechanisms of nucleophilic [SN2(P)] and electrophilic [SE2(P)} reactions have been analyzed, discussed and confirmed by experimental studies. SE2(P) reactions proceed with the retention of absolute configuration, while the SN2(P) reactions react with the inversion of the configuration at the phosphorus atom.

Stereoselective reactions of optically active derivatives of α-methylbenzylaminophosphine

A number of N-(α-methylbenzyl) phosphorus amides were synthesized, and their stereochemical properties were studied. Reactions of achiral chlorophosphines with optically active α-methylbenzylamine are accompanied by asymmetric induction at the phosphorus

Stereoselective reactions of chiral amines with racemic chlorophosphines

Racemic chlorophosphines react stereoselectively with chiral l-phenylethylamines or amino acid esters to give diastereomerically enriched aminophosphines 3, which were isolated as diastereomerically pure crystalline borane complexes. Oxidation, thionation, the reaction with methyl iodide provide optically active derivatives of aminophosphines. (R,S)- and (S,S)-stereomers of phosphinic acid amides were separated by crystallization and a flash-chromatography. The stereochemical properties of phosphorus acid amides were investigated. The mechanism of asymmetric induction at the trivalent phosphorus atom was rationalized.

Asymmetric synthesis of chiral N-(1-methylbenzyl)aminophosphines

The reactions of chlorophosphines 1 with (S)- or (R)-1-methylbenzylamines 2 proceed stereoselectively to give N-(1-methylbenzyl)aminophosphines 3, which were isolated as crystalline borane complexes with 100% diastereomeric purity. The absolute configuration of the new chiral compounds was established by X-ray analysis and chemical extrapolation.