A comparison of the asymmetric hydrogenation catalyzed by rhodium complexes containing chiral ligands with a binaphthyl unit and those with a 5,5′,6,6′,7,7′,8,8′-octahydro-binaphthyl unit
The chiral ligands H8-BINAPO and H8-BDPAB were synthesized by reacting chlorodiphenylphosphine with H8-BINOL and H8-BINAM, respectively. Applications of these ligands in the Rh-catalyzed enantioselective hydrogenation of a variety of (Z)-acetamido-3-arylacrylic acid methyl esters provided chiral amino acid derivatives with good to excellent enantioselectivities (H8-BINAPO: up to 84.0% e.e.; H8-BDPAB: up to 97.1% e.e.). In the hydrogenation of acetamidoacrylic acid, 99% e.e. was obtained when a [Rh(H8-BDPAB)]+ catalyst was used. The catalytic activities and enantioselectivities of [Rh(H8-BINAPO)]+ and [Rh(H8-BDPAB]+ are substantially better than those obtained with the corresponding rhodium catalysts containing BINAPO (up to 64% e.e.) and BDPAB (up to 92.6% e.e.).
Zhang, Fu-Yao,Kwok, Wai Him,Chan, Albert S.C.
p. 2337 - 2342
(2007/10/03)
Asymmetric synthesis of chiral amine derivatives through enantioselective hydrogenation with a highly effective rhodium catalyst containing a chiral bisaminophosphine ligand [2]
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Zhang,Pai,Chan
p. 5808 - 5809
(2007/10/03)
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