169437-76-7

Upstream product

• 1155850-63-7 (R_P,R_P)-1,2-bis[(methoxy)(phenyl)phosphino-P-borane]ethane 
• 917-54-4 methyllithium 
• 174511-99-0 (R)-(+)-[(O-methyl)methylphenylphosphinite]borane 
• 147127-50-2 (S,S)-(-)-1,2-bis(methoxyphenylphosphinoborane)ethane 
• 35512-87-9 dimethylphenylphosphine borane 

Downstream Products

• 1159593-68-6 (S,S)-1,2-bis[boranatophenyl(2-hydroxyethyl)phosphino]ethane 
• 1159593-71-1 C₂₄H₄₀B₂O₄P₂ 
• 1265629-92-2 C₂₆H₄₄B₂O₅P₂ 
• 1265629-88-6 C₂₂H₃₆B₂O₃P₂ 
• 17325-53-0 (R,R)-(-)-1,2-bis(methylphenylphosphino)ethane 

Relevant academic research and scientific papers

Olefin hydrogenation with rigid mono-P-stereogenic diphosphines: A flexible rhodium ring to rule them all?

The preparation of a rigid C1-symmetric P-stereogenic diphosphine series possessing a P-o-diphenylphosphinophenyl moiety and its use in RhI-catalyzed hydrogenation of benchmark olefins, is presented. This simplified ligand design, wh

Synthesis of enantiomerically pure P-stereogenic diphosphacrowns and their palladium complexes

A practical synthetic route for enantiomerically pure P-stereogenic diphosphacrowns was developed by using a P-stereogenic bisphosphine as a chiral building block. Their molecular structures were confirmed by NMR spectroscopy and X-ray crystallography. Complexation of the diphosphacrowns with palladium was carried out, and the corresponding palladium complexes were obtained. The P-stereogenic diphosphacrowns were applicable to the chiral ligand for the asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketone catalyzed by palladium. This reaction proceeded smoothly to afford the corresponding 1,4-addition products in high yield with good enantioselectivities.

Enantiodivergent synthesis of P-chirogenic phosphines

Several approaches for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines are described, using ephedrine methodology and phosphine borane chemistry. Firstly, both enantiomers of a tertiary phosphine can be obtained starting from the same oxazaphospholidine borane complex, prepared from (+)-ephedrine, when changing the order of addition of the organolithium reagents during the synthetic pathway. The second approach is based on the chlorophosphine boranes, which react with an organolithium reagent, to afford the corresponding phosphines with inversion of configuration. In the case where the chlorophosphine borane reacts with the t-butyl lithium reagent, a metal-halogen exchange occurs to afford the corresponding phosphide borane with retention of the configuration. The reaction of the phosphide borane with an alkyl halide leads to the same phosphine, but with the opposite configuration. Another approach depends on the diastereoselective preparation of the starting oxazaphospholidine borane complex from (-)-ephedrine, which leads according the case, to either one or the other enantiomer of a phosphine. Finally, the synthesis of (R,R)- and (S,S)-1,2-bis(methylphenylphosphino)ethane is also demonstrated using both enantiomers of the P-chirogenic diphosphinite diborane, which simultaneously allows the introduction of alkyl- or aryl substituents on the phosphorus atoms. In summary, these approaches show the great efficiency of the "ephedrine methodology" for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines, and bearing alkyl or aryl substituents.

Stereospecific construction of a trans-1,4-diphosphacyclohexane skeleton

(Chemical Equation Presented) trans-1,4-Diphosphacyclohexanes were successfully synthesized by the stereospecific intramolecular coupling reaction of the optically active bisphosphine. This is a new route for the construction of the trans-1,4-diphosphacyclohexane skeleton. A cis isomer was also prepared along with the trans isomer from a mixture of rac- and meso-bisphosphines. The coordinated boranes were easily removed to afford the corresponding 1,4-diphosphacyclohexanes.