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In an article, author is Lorraine, Shannen, once mentioned the application of 6372-42-5, Name is Cyclohexyldiphenylphosphine, molecular formula is C18H21P, molecular weight is 268.3331, MDL number is MFCD00046360, category is chiral-phosphine-ligands. Now introduce a scientific discovery about this category, COA of Formula: C18H21P.
Biaryl diphosphine ligands and their ruthenium complexes: Preparation and use for catalytic hydrogenation of ketones
Procedures for the preparation of the nucleophilic diphosphine ligands (R)-(4,4 ‘,6,6 ‘-tetramethoxybiphenyl-2,2 ‘-diyl)bis(diphenylphosphine) ((R)-Ph-Garphos, 2a) and (S)-(4,4 ‘,6,6 ‘-tetramethoxybiphenyl-2,2 ‘-diyl)bis(diphe-nylphosphine) ((S)-Ph-Garphos, 2b) were described. The ligands were used to prepare the ruthenium(II) Ph-Garphos complexes, chloro(p-cymene)(R)-(4,4 ‘,6,6 ‘-tetraamethoxybiphenyl-2,2 ‘-diyl)bis(diphenylphosphine)ruthenium(II) chloride ([RuCl(p-cymene)(R)-Ph-Garphos]Cl (3)) and chloro(p-cymene)(S)-(4,4 ‘,6,6 ‘-tetra-amethoxybiphenyl-2,2 ‘-diyl)bis(diphenylphosphine)ruthenium(II) chloride ([RuCl(p-cymene)(S)-Ph-Garphos]Cl (4)). In the presence of the chiral diamine co-ligands (1R,2R)-1,2-diphenylethane-1,2-diamine (R,R-DPEN) and (1S,2S)-1,2-diphenylethane-1,2-diamine (S,S-DPEN), complexes 3 and 4 were found to be catalyst precursors for the enantioselective reduction of aryl ketones under mild conditions (room temperature and 3-4 atm of H-2). The chiral alcohols were isolated in moderate to good yields and with enantioselectivities of up to 93%. The ru-thenium complexes chloro(p-cymene)(R)-(4,4 ‘,6,6 ‘-tetramethoxybiphenyl-2,2 ‘-diyl)bis(bis(3,5-dimethylphenyl)phosphine)ruthenium(II) chloride ([RuCl(p-cymene)(R)-Xyl-Garphos]Cl (5)) and chloro(p-cymene)(S)-(4,4 ‘,6,6 ‘-tetramethoxybiphenyl-2,2 ‘-diyl)bis(bis(3,5-dimethylphenyl)-phosphine)ruthenium(II) chloride ([RuCl(p-cymene)(S)-Xyl-Garphos]Cl (6)) were also prepared and used as catalyst precursors for the hydrogenation of aryl ketones in the presence of (R,R)-DPEN and (S,S)-DPEN. Significant improvements in the enantioselectivities of the alcohols (up to 98% ee.) were afforded. A combination of 6 and (S,S)-DPEN afforded (R)-1-(3-methoxyphenyl)ethanol in 89% yield and with 95% ee which was shown to be a suitable precursor for the preparation of (S)-rivastigmine.
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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