61478-29-3

Basic information

• Product Name: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine
• Synonyms: (2S,4S)-(-)-4-DIPHENYLPHOSPHINO-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2S,4S)-4-(DIPHENYLPHOSPHINO)-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2S,4S)-(-)-DIPHENYLPHOSPHINO 2-DIPHENYLPHOSPHINOMETHYL PYRROLIDINE;(2S,4S)-PPM;(-)-PPM;PPM;(S)-4-Diphenylphosphino-2-(Diphenylphosphino)pyrrolidine;(2S 4S)-(-)-4-(DIPHENYLPHOSPHINO)-2-(DI&
• CAS NO: 61478-29-3
• Molecular Formula: C₂₉H₂₉NP₂
• Molecular Weight: 453.49
• Product Categories: API intermediates;Chiral Phosphine;PM Series
• Mol File: 61478-29-3.mol

Chemical Properties

• Melting Point: 102-104 °C(lit.)
• Boiling Point: 575.753°C at 760 mmHg
• Flash Point: 302.005°C
• Appearance: white/Powder
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: 0-6°C
• PKA: 9.87±0.10(Predicted)
• Sensitive: air sensitive
• CAS DataBase Reference: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine(61478-29-3)
• EPA Substance Registry System: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine(61478-29-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 61478-29-3(Hazardous Substances Data)

Usage

Uses

Used in Metal Catalysis:
(2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine is used as a ligand in metal catalysis for its capacity to coordinate with transition metals, forming stable complexes that facilitate a range of organic transformations. The phosphine groups in the compound play a crucial role in this coordination, enhancing the efficiency and selectivity of catalytic processes.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine is utilized as a chiral ligand to induce asymmetry in reactions. Its chiral nature allows for the creation of complex organic molecules with high levels of stereochemical control, which is essential for the production of enantiomerically pure compounds, often required in pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
(2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine is used as a key intermediate in the synthesis of pharmaceuticals, particularly for the development of enantiomerically pure drugs. (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine's ability to induce chirality in reactions is invaluable in creating the desired stereochemistry of drug molecules, which can significantly impact their efficacy and safety.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine is employed as a ligand in the synthesis of chiral agrochemicals. The precise control over the stereochemistry of these compounds is crucial for their biological activity and selectivity towards target pests, reducing potential environmental impact.
Used in Research and Development:
(2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine is also used in research and development settings as a tool to explore new catalytic systems and asymmetric synthetic methodologies. Its unique properties make it an attractive candidate for studying the fundamental aspects of metal-ligand interactions and their influence on reaction outcomes.

InChI:InChI=1/C29H29NP2/c1-5-13-25(14-6-1)31(26-15-7-2-8-16-26)23-24-21-29(22-30-24)32(27-17-9-3-10-18-27)28-19-11-4-12-20-28/h1-20,24,29-30H,21-23H2/t24-,29-/m0/s1

Upstream product

• 33996-30-4 trans-4-hydroxy-L-proline ethyl ester hydrochloride 
• 51-35-4 4R-4-hydroxyproline 
• 1079-66-9 chloro-diphenylphosphine 
• 98-59-9 p-toluenesulfonyl chloride 
• 37813-30-2 (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 61478-27-1 (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine 
• 61478-28-2 (2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine 

Downstream Products

• 64145-67-1 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-pivaloylpyrrolidine 
• 74571-28-1 (2S,4S)-4-Diphenylphosphanyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine-1-carboxylic acid (4-chloro-phenyl)-amide 
• 74571-31-6 (2S,4S)-4-Diphenylphosphanyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine-1-carboxylic acid (4-nitro-phenyl)-amide 
• 74571-27-0 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-phenylcarbamoylpyrrolidine 
• 80630-78-0 CBZ-(R)-Pro-PPM 
• 66505-76-8 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-formylpyrrolidine 
• 80630-76-8 CBZ-(R)-Ala-PPM 
• 80630-75-7 CBZ-(S)-Ala-PPM 
• 80630-79-1 CBZ-(S)-Val-PPM 
• 80630-74-6 CBZ-(S)-Phe-PPM 
• 80630-81-5 CBZ-(S)-Phe-(S)-Val-PPM 
• 74571-33-8 (2S,4S)-4-Diphenylphosphanyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine-1-carboxylic acid allylamide 
• 74571-34-9 (2S,4S)-4-Diphenylphosphanyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine-1-carboxylic acid cyclohexylamide 
• 74571-29-2 (2S,4S)-4-Diphenylphosphanyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine-1-carboxylic acid (4-bromo-phenyl)-amide 

Relevant articles and documents

Efficient preparation of optically active (S)-(-)-3-methyl-γ-butyrolactone by catalytic asymmetric hydrogenation using chiral N-substituted pyrrolidinebisphosphine rhodium complexes

(S)-(-)-2-Methyl succinamic acid, which is a good precursor of (S)-(-)-3-methyl-γ-butyrolactone, can be prepared by homogeneous asymmetric hydrogenation of 2-methylene succinamic acid catalyzed by (2S,4S)-N-substituted-4-(diphenylphosphino)-2-[(diphenylphosphino)-meth yl]pyrrolidine-rhodium complexes. Various N-substituted pyrrolidine-bisphosphines were synthesized to find the optimum ligand for this purpose and to compare the effects of the N-substituents.

Asymmetric Hydrogenation of 3,4-Methylenedioxy-α-acetamidocinnamic Acid Using Newly Developed Silica Gel-Supported Chiral Rhodium(I)-Phosphine Complexes

The asymetric hydrogenation of 3,4-methylenedioxy-α-acetamidocinnamic acid was carried out in the presence of a chiral Rh(l)-complex of (2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (BPPM) adsorbed on hydrophobic silica

Transition-Metal-Catalyzed Asymmetric Organic Synthesis via Polymer-Attached Optically Active Phosphine Ligands. 5. Preparation of Amino Acids in High Optical Yield via Catalytic Hydrogenation

Two new optically active phosphinopyrrolidine monomers were prepared by the reaction of (2S,4S)-4-(diphenylphosphino)-2-pyrrolidine and (2R,4R)-4-(diphenylphosphino)-2-pyrrolidine with acryloyl chloride to give N-acryloyl-(2S,4S)-4-(diphenylphosphino)-2-pyrrolidine (1) and N-acryloyl-(2R,4R)-4-(diphenylphosphino)-2-pyrrolidine (2).Copolymerization of 1 and 2 with hydrophilic comonomers and a divinyl monomer provided cross-linked insoluble polymers containing 3-5percentof 1 or 2 that would swell in polar solvents.Exchange of rhodium (I) onto the polymer gave catalysts which were active for the asymmetric hydrogenation of N-acyl α-amino acids in high optical yields, the phosphine derived from the enantiomer of the naturally occurring 4-hydroxyproline giving (S)-amino acids.The catalysts could be reused with no loss in selectivity by simple filtration.

Asymmetric Hydrogenation of Prochiral Olefins Catalyzed by Rhodium Complexes with Chiral Pyrrolidinodiphosphines. Crucial Factors for the Effective Asymmetric Induction

Remarkable effects of hydrogen pressure on the stereoselectivity were observed in the asymmetric hydrogenations of itaconic acid, α-(acylamino)acrylic acid, and their derivatives catalyzed by rhodium complexes of chiral pyrrolidinodiphosphines.Effects of added triethylamine on the pressure dependency of stereoselectivity were also studied.Marked differences in the direction of asymmetric induction were found in the asymmetric hydrogenations of the methylsuccinic acid precursors itaconic acid, citraconic acid, and mesaconic acid.This result clearly indicates that the chiral recognition by the rhodium catalyst is extremely sensitive to the stereochemistry of the prochiral olefins.Possible mechanisms are discussed on the basis of these results. 31PNMR studies on the key intermediates in asymmetric hydrogenations have revealed that the mode of the bidentate complexation of the prochiral substrates is extremely regioselective.The "induced-fit" phenomena of the chiral rhodium complex were observed.A possible mechanism for the chiral recognition of enantiofaces in the chiral coordination sphere is proposed.