1103533-85-2

Usage

Uses

Used in Organometallic Chemistry:
(S)-2-(Diphenylphosphino)-1-phenylethylamine, min. 97% is used as a ligand for the synthesis of transition metal complexes. Its chiral amine and phosphine group provide unique coordination properties, enabling the formation of stable and functional metal complexes with potential applications in catalysis, materials science, and pharmaceuticals.
Used in Asymmetric Catalysis:
In the field of asymmetric catalysis, (S)-2-(Diphenylphosphino)-1-phenylethylamine, min. 97% is employed as a chiral ligand to induce enantioselectivity in various organic reactions. Its unique structure allows for the selective formation of enantiomers, which is crucial for the development of chiral drugs and agrochemicals.
Used in Research and Development:
Due to its high purity and versatile reactivity, (S)-2-(Diphenylphosphino)-1-phenylethylamine, min. 97% is extensively used in research and development for the discovery and optimization of new chemical reactions, synthesis routes, and applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-2-(Diphenylphosphino)-1-phenylethylamine, min. 97% is utilized as a building block for the synthesis of chiral pharmaceuticals and drug candidates. Its unique structure and reactivity enable the development of novel compounds with potential therapeutic applications.
Used in Materials Science:
(S)-2-(Diphenylphosphino)-1-phenylethylamine, min. 97% is also employed in materials science for the synthesis of functional materials with specific properties, such as chiral catalysts, sensors, and optoelectronic devices. Its high purity and versatile reactivity contribute to the development of advanced materials with potential applications in various fields.

Upstream product

• 4559-70-0 Diphenylphosphine oxide 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 829-85-6 diphenylphosphane 
• 110143-62-9 (S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester 
• 100-52-7 benzaldehyde 
• 479687-23-5 1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide 
• 479687-18-8 2-oxo-4-phenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester 
• 117049-14-6 tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate 
• 20989-17-7 (2S)-2-phenylglycinol 
• 2935-35-5 (S)-2-phenylglycine 
• 171001-99-3 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl 4-methylbenzenesulfonate 
• 1239019-97-6 (S)-tert-butyl (2-(diphenylphosphino)-1-phenylethyl)carbamate 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 

Downstream Products

• 1853342-57-0 (S)-N-(2-(diphenylphosphanyl)-1-phenylethyl)-3,5-bis(trifluoromethyl)benzamide 
• 1269668-21-4 C₂₇H₂₅N₂PS 

Relevant academic research and scientific papers

Tunable Bifunctional Phosphine-Squaramide Promoted Morita-Baylis-Hillman Reaction of N-Alkyl Isatins with Acrylates

A series of highly tunable bifunctional phosphine-squaramide H-bond donor organocatalysts 6 has been synthesized from inexpensive and commercially available β-amino alcohols in moderate yields. Catalyst 6 can efficiently promote the asymmetric Morita-Baylis-Hillman (MBH) reaction of N-alkyl isatins with acrylate esters providing the chiral 3-substituted 3-hydroxy-2-oxindoles in good yields and enantioselectivities (up to 93 yield and 95 ee), in which the challenging substrate tert-butyl acrylate 9d, provided the best ee value to date. Moreover, this methodology was applied successfully in the synthesis of chiral cyclic spiropyrrolizidineoxindole and γ-butyrolactone derivatives without enantioselectivity deterioration. The possible mechanism of this MBH reaction was also investigated by 31PNMR, ESI-MS and KIE studies. The KIE experiments show that the electrophilic addition of N-methyl isatin to the complex of acrylate ester and phophine-squaramide is the rate-determing step of the asymmetric MBH reaction.

Preparation method and application of chiral N-(2-(phosphoryl)-1-phenethyl)amide

The invention discloses a preparation method of chiral N-(2-(phosphoryl)-1-phenethyl) amide and application of the chiral N-(2-(phosphoryl)-1-phenethyl) amide. A method is provided for the high yield,high enantioselectivity preparation of the chiral N-(2-

Chiral phosphine-phosphoramidite ester ligand as well as preparation method and application thereof

The invention provides a method for preparing a phosphine-phosphoramidite ester ligand from a chiral beta-aminophosphine intermediate and an application of the phosphine-phosphoramidite ester ligand in an asymmetric reaction. Chiral N-(2-(phosphoryl)-1-phenethyl) amide is prepared from the chiral beta-aminophosphine intermediate through an asymmetric hydrogenation reaction of (Z)-(alpha-aryl-beta-phosphoryl) alkenyl amide, and then hydrolysis reduction. The preparation method comprises the following steps: dissolving newly-prepared chlorinated phosphite in toluene, adding a solution formed by dissolving the chiral phosphine-amine compound and triethylamine in toluene into an ice-water bath according to a molar ratio of the chiral phosphine-amine compound to the chlorinated phosphite to the triethylamine of 1: (1-2): (3-5), heating the reaction solution to 18-25 DEG C, stirring and reacting for 10-30 hours, filtering, and carrying out column chromatography to remove the solvent, and recrystallizing to obtain the required phosphine-phosphoramidite ligand. According to the present invention, the asymmetric hydrogenation reaction of the catalyst formed by the ligand and the metal precursor on the double bonds such as C = C, C = N, C = O and the like can achieve the enantioselectivity of 99%; the catalyst is high in activity, and TON reaches up to 10000.

Rh-Catalyzed Asymmetric Hydrogenation of (Z)-β-Phosphorylated Enamides: Highly Enantioselective Access to β-Aminophosphines

A catalytic asymmetric hydrogenation of β-phosphorylated enamides for enantioselective access to optically active β-aminophosphine derivatives is reported. Critical to the success of this method was the employment of rhodium catalysis in concert with an u

β-Amino Phosphine Mn Catalysts for 1,4-Transfer Hydrogenation of Chalcones and Allylic Alcohol Isomerization

Mn complexes with amino acid derived PN ligands were used in the catalytic transfer hydrogenation (TH) of ketone and chalcone substrates in 2-propanol with mild heating. Moreover, chalcones are reduced selectively to the saturated ketone at short times and can be fully converted to the alcohol when reactions are prolonged. The mechanism of chalcone reduction was briefly considered. Allylic alcohols are not reactive in 2-propanol, but quantitative isomerization occurs in toluene. Thus, we suspect that the allylic alcohols are dehydrogenated and the resulting ketone is formed through a direct 1,4-hydrogenation of the chalcone. Finally, several other related ligands that have been used in Mn-based TH reactions were explored to test the viability of ligand design in favoring chemoselectivity. The β-amino phosphine ligands proved most effective in this regard.

Asymmetric kinetic resolution of sulfides for the construction of unsymmetric sulfides and chiral 3,3-disubstituted oxindoles

A range of 3,3-disubstituted oxindoles accessed using para-quinone methides derived from isatins with thiols were used for the formation of unsymmetrical disulfides, and 3,3-disubstituted oxindoles with a chiral quaternary carbon center and unsymmetric di

Novel chiral sulfinamide phosphines: Valuable precursors to chiral β-aminophosphines

Starting from commercially available aldehyde and chiral tert-butanesulfinamide, a series of chiral sulfinamide phosphines (Xiao-Phos) were synthesized via a two-step condensation-nucleophilic addition procedure. In most cases, nucleophilic addition of th

Synthesis of iron P-N-P' and P-NH-P asymmetric hydrogenation catalysts

Complexes of the type mer,trans-[Fe(P-N-P)(CO)2Br]BF4 are known to be precatalysts for the asymmetric direct hydrogenation of ketones and imines. Employing related ligand scaffolds, we successfully generated and tested the series of three new precatalysts [Fe(PCy2CH2CH-NCH(R)CH2PPh2)(CO)2Br]BF4 with chirality derived from (S)-amino alcohols with phenyl, benzyl, and isopropyl substituents (R), yielding fairly active and selective systems. For the reduction of acetophenone to (S)-1-phenylethanol turnover frequencies up to 920 h-1 and up to 74% enantiomeric excess at 50 °C and 5-25 atm of H2 were obtained. We found, however, that placing these large groups R next to nitrogen was found to be deleterious to catalytic activity. Extending the scope of the ligand structure, we then developed a series of six P-N-P and five P-NH-P systems starting with o-diphenylphosphinobenzaldehyde and the phosphine-amines PPh2CHR1CHR2NH2 (R1 = H, Ph, CH2Ph, iPr with R2 = H or R1 = Me, Ph with R2 = Ph) as well as their corresponding [Fe(P-N-P)(NCMe)3][BF4]2 and [Fe(P-NH-P)(NCMe)3][BF4]2 complexes, which were not catalytically active. Finally, we made the new achiral iron complex mer,cis-Fe(PPh2(o-C6H4)CHNCH2CH2PPh2)(CO)Br2, which was active for the direct hydrogenation of acetophenone, achieving turnover frequencies of 800 h-1 at 50°C and 25 atm of H2.

Asymmetrie [3+2] cycloadditions of allenoates and dual activated olefins catalyzed by simple bifunctional N-acyl aminophosphines

(Figure Presented) Bifunctional catalyst: Simple bifunctional N-Acyl aminophosphines such as 1 were developed to catalyze the first asymmetric [3+2] cycloaddition between allenoates and dual activated olefins. The cycloaddi- tion reactions afford multifun