77876-39-2

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-(-)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE is used as a ligand for asymmetric hydrogenation reactions in the pharmaceutical industry. Its application is crucial for the production of enantiomerically pure compounds, which are essential for the development of many drugs with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2S,4S)-(-)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE is employed as a ligand for various asymmetric catalytic reactions, including the hydrogenation of ketones and alkenes. Its use contributes to the synthesis of chiral compounds with high enantioselectivity and yield, which is vital for the production of specialty chemicals and fine chemicals.
Used in Research and Development:
(2S,4S)-(-)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE is also utilized in research and development settings for the study of asymmetric catalysis and the development of new synthetic methods. Its unique properties make it a valuable tool for chemists working on the design and optimization of enantioselective reactions.

InChI:InChI=1/C29H30P2/c1-24(30(26-15-7-3-8-16-26)27-17-9-4-10-18-27)23-25(2)31(28-19-11-5-12-20-28)29-21-13-6-14-22-29/h3-22,24-25H,23H2,1-2H3/t24-,25-/m0/s1

Upstream product

• 603-35-0 triphenylphosphine 
• 96243-67-3 (2S,4S)-pentane-2,4-diyl bis-(4-methylbenzenesulfonate) 
• 1079-66-9 chloro-diphenylphosphine 
• 190671-79-5 (4R,6R)-4,6-dimethyl-(1,3,2)-dioxathian-2,2-dioxide 
• 41593-58-2 diphenylphosphineborane 
• 145130-18-3 lithium diphenylphosphido borane 
• 4559-70-0 Diphenylphosphine oxide 
• 108-86-1 bromobenzene 
• 14367-67-0 2-methyl-3-phenylpropionic acid 
• 15475-27-1 potassium diphenylphosphine 
• 4376-01-6 sodium diphenylphosphide 

Relevant academic research and scientific papers

Ni-Catalyzed enantioselective reductive arylcyanation/cyclization of: N -(2-iodo-aryl) acrylamide

A Ni/(S,S)-BDPP-catalyzed intramolecular Heck cyclization of N-(2-iodo-aryl) acrylamide with 2-methyl-2-phenylmalononitrile was developed to give oxindoles with good enantioselectivities. We found that utilizing such an electrophilic cyanation reagent cou

RHODIUM CATALYST AND METHOD FOR PRODUCING AMINE COMPOUND

[Problem] Provision of a superior rhodium catalyst and a production method of amine compound. [Solving Means] A rhodium complex coordinated with a compound represented by the formula

Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation

Chiral diphosphine ligands analogous to bdpp have been synthesized and tested in order to study the effect of the electronic nature of the ligands in Rh-catalyzed asymmetric hydrogenation of some prochiral olefins. The results are compared with those obtained with the analogous unsubstituted ligand (bdpp). The rhodium-catalyzed asymmetric hydrogenation of olefins was influenced by ligand-based electronic effects, as well as substrate based ones. Excellent ee's (up to 98.3%) have been obtained in the rhodium-catalyzed hydrogenation of (Z)-α-acetamidocinnamic acids and esters.

One-pot synthesis of a novel C1-symmetric diphosphine from 1,3-cyclic sulfate. Asymmetric hydroformylation of styrene

Preparation of a novel homochiral diphosphine with C1-symmetry from the cyclic sulfate of (2R.4R)-2.4-pentanediol is reported. Reaction of a lithium phosphide salt with the cyclic sulfate affords a γ-phospholylsulfate which can be converted to

Process for producing optically active benzhydrol compounds

A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: STR1 wherein R1 to R10 each represents H, OH, C1-4 alkyl, C1-4 alkoxy, C1-4 alkanoyl, etc., R2 and R3, and R8 and R9 may form --CH=CH--CH=CH--, or any two of R1 to R9 adjacent to each other may be bonded to thereby form --OCH2 O-- or --(CH2)3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.

An Asymmetric Hydrogenation Sysytem Breeding Its Own Counter-configurated Ligand

A homogeneous catalytic system based on Ruthenium-Skewphos complexes is presented, which breeds enantioselectively a precursor for the synthesis of Skewphos.In contrast to the known "self breeding" system of Prophos, this system generates the precursor for the opposite enantiomer of the ligand to enable access to both enantiomer of Skewphos after one and two cycles, respectively.

A FACILE METHOD FOR THE PREPARATION OF 2,4-BIS(DIPHENYLPHOSPHINO)PENTANE(BDPP) ENENTIOMERS AND THEIR APPLICATION IN ASYMMETRIC HYDROGENATION

Asymmetric heterogeneous hydrogenation of acetylacetone was applied for the preparation of both enantiomers (2R,4R and 2S,4S) of 2,4-bis(diphenylphosphino)pentane (BDPP).Among the chiral phosphine prepared up to now BDPP appears to be unique in the sense that its rhodium(I) complexes serve as effective homogeneous asymmetric hyrogenation catalysts not only for the reduction Z-α-amidoacrylic acids but also for the reduction of α-ethylstyrene, acetophenone, and acetophenonebenzylimine.The analogous phosphinite ligand BDPOP yields a less active catalyst

Asymmetric Synthesis. Asymmetric Catalytic Hydrogenation Using Chiral Chelating Six-Membered Ring Diphosphines

Rhodium(I) catalysts formed by the two chiral chelating six-membered ring diphosphines, 2,4-bis(diphenylphosphino)pentane (skewphos) and 1,3-bis(diphenylphosphino)butane (chairphos), are efficient catalysts for the hydrogenation of amino acid precursors.The two chiral phosphines differ in that skewphos probably adopts a chiral conformation whereas chairphos probably adopts an achiral conformation.This comparison evidences the importance of ring conformations in determining optical yields.The mechanism of asymmetric hydrogenation is discussed, and a number of particular and general conclusions are drawn which may prove useful in predicting optical yields from asymmetric synthesis.