2, 2'-bis(diphenylphosphino)-1, 1'-binaphthyl(binap) : A new atropisomeric bis(triaryl)phosphine. synthesis and its use in the rh(l)-catalyzed asymmetric hydrogenation of α-(acylamino)acrylic acids |
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Authors: | A. Miyashita H. Takaya T. Souchi R. Noyori |
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Affiliation: | Chemical Materials Center, Institute for Molecular Science, Okazaki National Research Institutes, Okazaki 444 Japan;Department of Chemistry, Nagoya University, Chikusa, Nagoya 464, Japan |
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Abstract: | Racemic 2, 2'-bis(diphenylphosphino)-l, 1'-binaphthyl has been synthesized from 2, 2'-dihydroxy-l, l'-binaphthyl in two steps and resolved into optically pure (R)-(+) and (S) (-) enantiomers by the use of (+)-di-μ-chlorobis[(S)-N,N-dimethyl-α-phenylethylamine-2C,N]dipalladium. This new axially dissymmetric bis(triaryl)phosphine serves as an excellent ligand for Rh(l)-catalyzed asymmetric hydrogenations of α-(acylamino) acrylic acids or esters. Factors controlling the enantioselectivity and mechanistic aspects are discussed on the basis of the 31P-NMR measurements |
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