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À propos de : Lipase-Catalyzed Transesterification of2-Hydroxy-2-(pentafluorophenyl)acetonitrile Leading to (1R,2R)-and (1S,2S)-Bis(pentafluorophenyl)ethane-1,2-diol        

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  • Lipase-Catalyzed Transesterification of2-Hydroxy-2-(pentafluorophenyl)acetonitrile Leading to (1R,2R)-and (1S,2S)-Bis(pentafluorophenyl)ethane-1,2-diol
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  • Optically pure (1R,2R)- and (1S,2S)-1,2-bis(pentafluorophenyl)ethane-1,2-diol (1) were synthesizedfrom key intermediates (R)- and (S)-2-hydroxy-2-(pentafluorophenyl)acetonitrile (2), both of whichwere prepared by the lipase LIP-catalyzed transesterification (E = 465). The absolute configurationof (S)-2 was determined by X-ray structural analysis after transformation into (S)-α-cyano-2,3,4,5,6-pentafluorobenzyl (S)-6-methoxy-α-methyl-2-naphthaleneacetate (S,S)-9. In addition, the crystalstructure of (S,S)-9 has an interesting well-ordered packing pattern which shows face-to-facestacking interactions and end-to-end parallel contacts between the pentafluorophenyl and 6-methoxynaphthyl groups of the adjacent molecules.
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