136705-65-2 Usage
Description
(R,R)-I-PR-DUPHOS is a type of chiral phosphine ligand that belongs to the DUPHOS family. It is characterized by its optical rotation deviation of ± 13, which is an essential property for its applications in various chemical reactions.
Uses
1. Used in Catalysts:
(R,R)-I-PR-DUPHOS is used as a ligand in the synthesis of catalysts for various chemical reactions. Its chiral nature and optical rotation deviation make it a highly efficient and privileged ligand, similar to DuPhos and BPE ligands.
2. Used in Asymmetric Catalysis:
In the field of asymmetric catalysis, (R,R)-I-PR-DUPHOS is employed as a ligand to enhance the selectivity and enantioselectivity of the reactions. Its unique properties allow for the creation of chiral molecules with high precision, which is crucial in the synthesis of pharmaceuticals and other fine chemicals.
3. Used in Homogeneous Catalysis:
(R,R)-I-PR-DUPHOS is also utilized in homogeneous catalysis, where it acts as a ligand to improve the activity and selectivity of metal catalysts. This application is particularly relevant in the production of specialty chemicals and materials with specific properties.
4. Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R,R)-I-PR-DUPHOS is used as a ligand for the development of chiral catalysts that facilitate the synthesis of enantiomerically pure drugs. The high efficiency and selectivity of this ligand contribute to the production of drugs with improved efficacy and reduced side effects.
5. Used in Chemical Research:
(R,R)-I-PR-DUPHOS is also employed in academic and industrial research settings, where it is used to study the mechanisms of various chemical reactions and to develop new catalytic systems with enhanced performance. Its unique properties make it a valuable tool for advancing the field of chemistry and materials science.
Reaction
The DUPHOS family of catalysts is highly efficient for the asymmetric hydrogenation of various substituted acetamidoacrylates and enol acetates yielding products of high enantiomeric excesses. Efficient ligand for the asymmetric hydrogenation of tetrasubstituted enamides.
Forms superior catalysts for asymmetric reductive aminations.
Catalyst used for the asymmetric hydrogenation of enol phosphonates.
A novel enantioselective synthesis of β-amino alcohols and 1,2-diamines.
Check Digit Verification of cas no
The CAS Registry Mumber 136705-65-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,6,7,0 and 5 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 136705-65:
(8*1)+(7*3)+(6*6)+(5*7)+(4*0)+(3*5)+(2*6)+(1*5)=132
132 % 10 = 2
So 136705-65-2 is a valid CAS Registry Number.
InChI:InChI=1/C26H44P2/c1-17(2)21-13-14-22(18(3)4)27(21)25-11-9-10-12-26(25)28-23(19(5)6)15-16-24(28)20(7)8/h9-12,17-24H,13-16H2,1-8H3/t21-,22-,23-,24-/m1/s1
136705-65-2Relevant articles and documents
Diastereoselective Coordination of P-Stereogenic Secondary Phosphines in Copper(I) Chiral Bis(phosphine) Complexes: Structure, Dynamics, and Generation of Phosphido Complexes
Gibbons, Sarah K.,Valleau, Christopher R. D.,Peltier, Jesse L.,Cain, Matthew F.,Hughes, Russell P.,Glueck, David S.,Golen, James A.,Rheingold, Arnold L.
, p. 8854 - 8865 (2019)
Diastereoselective coordination of racemic secondary phosphines (PHRR′) to Cu(I) precursors containing chiral bis(phosphines) (diphos*) was explored as a potential route to P-stereogenic phosphido complexes. Reaction of [Cu(NCMe)4][PF6] with chiral bis(phospholanes) gave [Cu(diphos*)2][PF6] (diphos? = (R,R)-Me-DuPhos (1), (R,R)-Et-DuPhos (2), or (R,R)-Me-FerroLANE) (3)) or the mono(chelates) [Cu(diphos*)(NCMe)n][PF6] (diphos? = (R,R)-i-Pr-DuPhos, n = 2 (4); diphos? = (R,R)-Me-FerroLANE, n = 1 (5)). Treatment of [Cu(NCMe)4][PF6] with diphos? and PHMe(Is) (Is = 2,4,6-(i-Pr)3C6H2) gave mixtures of diastereomers of [Cu((R,R)-i-Pr-DuPhos)(PHMe(Is))(NCMe)][PF6] (6) and [Cu((R,R)-Me-FerroLANE)(PHMe(Is))][PF6] (7); two of the three expected isomers of the bis(secondary phosphine) complexes [Cu((R,R)-i-Pr-DuPhos)(PhHP(CH2)nPHPh)][PF6] (n = 2 (8); n = 3 (9)) were formed preferentially in related reactions. Reaction of the halide-bridged dimers [Cu((R,R)-i-Pr-DuPhos)(X)]2 or [Cu((R,R)-Me-FerroLANE)(I)]2 with PHMe(Is) gave the labile adducts Cu((R,R)-i-Pr-DuPhos)(PHMe(Is))(X) (X = Cl (10), Br (11), I (12)) and Cu((R,R)-Me-FerroLANE)(PHMe(Is))(I) (13). Complexes 1, 6, and 8-11 were structurally characterized by X-ray crystallography. Variable temperature NMR studies of 6 and 8 showed that the secondary phosphine ligands underwent reversible dissociation. Deprotonation of 6 or 7 generated the P-stereogenic phosphido complexes Cu(diphos*)(PMeIs) (diphos? = (R,R)-i-Pr-DuPhos (14) or (R,R)-Me-FerroLANE) (17)), observed by 31P NMR spectroscopy, but decomposition also occurred. Density functional theory calculations were used to characterize the diastereomers of thermally unstable 17 and the inversion barrier in a model copper-phosphido complex. These observations provided structure-property relationships which may be useful in developing catalytic asymmetric reactions involving secondary phosphines and P-stereogenic copper phosphido intermediates.
C2-symmetric bis(phospholanes) and their use in highly enantioselective hydrogenation reactions
Burk, Mark J.
, p. 8518 - 8519 (2007/10/02)
-
