Catalytic Hydrogenation of Acetophenone with Hydrogen Transfer over Chiral Diamine Rhodium(I) Complexes |
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Authors: | Nindakova L O Shainyan B A Belonogova L N |
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Institution: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia |
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Abstract: | The catalytic activity and stereoselectivity of Rh(I) complexes with C
2-symmetric chiral diamines, (4S,5S)-3,4-isopropylidenedioxy-1,4-butanediamine and (4S,5S)-N,N,N',N'-tetramethyl-3,4-isopropylidenedioxy-1,4-butanediamine skeletal analogs of 2,3-dihydroxy-2,3-O-isopropylidene-1,4-bis(diphenylphosphino)butane (DIOP)], were studied in hydrogen transfer from 2-propanol to acetophenone in the presence of KOH or t-BuOK. The product, (S)-(-)-2-phenylethanol, was thus obtained with an optical yield of 67%. Covalent chloride rhodium complexes with the above ligands give rise to the same stereoisomer, whereas the opposite stereoselectivity is observed under catalysis by cationic trifluoromethanesulfonate rhodium(I) complexes. X-Ray phase analysis showed formation of nanosize particles in the precipitate of metallic rhodium. |
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