(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane  (Synonyms: (S,S)-Ph-BPE)

(+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane ((S,S)-Ph-BPE) is a chiral bisphosphine ligand and catalyst. (+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane acts as a chiral ligand in rhodium-catalyzed reductive hydroformylation of alkenyl boronic esters, enabling enantiodivergent synthesis of chiral γ-boryl alcohols. (+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane forms chiral nickel-phosphine complexes to mediate asymmetric hydrogenation of aliphatic γ- and δ-keto acids; protons promote substrate C₌O bond activation and stereoselectivity control via hydrogen bonding. (+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane forms a monodentate nickel complex, which serves as the active species for asymmetric hydrogenation of aliphatic keto acids^[1][2].

(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane ((S,S)-Ph-BPE) acts as a chiral ligand in Rh-catalyzed reductive hydroformylation of aryl-substituted alkene 1,2-diboronic esters, enabling formation of chiral 1,3-diols^[1].
(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane induces enantiodivergence in Rh-catalyzed reductive hydroformylation of alkene 1,2-diboronic esters and α-substituted alkenyl boronic esters via energy differences in the enantio-determining olefin insertion transition states, producing chiral products with opposite configurations^[1].
(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane (0.0133-1 mol%; 12-24 h) forms a highly active homogeneous chiral nickel-phosphine complex that catalyzes the asymmetric hydrogenation of aliphatic γ- and δ-ketoacids, including biomass-derived levulinic acid, to produce chiral lactones with up to 98% yield, 99% ee, and a maximum substrate-to-catalyst ratio of 7500^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

506.60

C₃₄H₃₆P₂

824395-67-7

Solid

White to off-white

P1([C@H](C2=CC=CC=C2)CC[C@H]1C3=CC=CC=C3)CCP4[C@H](C5=CC=CC=C5)CC[C@H]4C6=CC=CC=C6

Room temperature in continental US; may vary elsewhere.

4°C, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Yu Y, et al. Enantiodivergent Rh-Catalyzed Reductive Hydroformylation of Alkenyl Boronic Esters. Angew Chem Int Ed Engl. 2026;65(2):e20602.  [Content Brief]

  [2]. Deng CQ, et al. Proton-Promoted Nickel-Catalyzed Asymmetric Hydrogenation of Aliphatic Ketoacids. Angew Chem Int Ed Engl. 2022;61(15):e202115983.  [Content Brief]