In an article, author is Muldoon, Jake A., once mentioned the application of 1486-28-8, SDS of cas: 1486-28-8, Name is Methyldiphenylphosphine, molecular formula is C13H13P, molecular weight is 200.2161, MDL number is MFCD00008508, category is chiral-phosphine-ligands. Now introduce a scientific discovery about this category.
Inversion of Configuration at the Phosphorus Nucleophile in the Diastereoselective and Enantioselective Synthesis of P-Stereogenic syn-Phosphiranes from Chiral Epoxides
Nucleophilic substitution results in inversion of configuration at the electrophilic carbon center (S(N)2) or racemization (S(N)1). The stereochemistry of the nucleophile is rarely considered, but phosphines, which have a high barrier to pyramidal inversion, attack electrophiles with retention of configuration at P. Surprisingly, cyclization of bifunctional secondary phosphine alkyl tosylates proceeded under mild conditions with inversion of configuration at the nucleophile to yield P-stereogenic syn-phosphiranes. DFT studies suggested that the novel stereochemistry results from acid-promoted tosylate dissociation to yield an intermediate phosphenium-bridged cation, which undergoes syn-selective cyclization.
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Reference:
Phosphine ligand,
,Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate