Lipase-catalyzed transesterification of 2-hydroxy-2- (pentafluorophenyl)acetonitrile leading to (1R,2R)-and (1S,2S)-bis (pentafluorophenyl)ethane-1,2-diol

Takashi Sakai, Yasushi Miki, Masashi Tsuboi, Hiroaki Takeuchi, Tadashi Ema, Kenji Uneyama, Masanori Utaka

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33 Citations (Scopus)

Abstract

Optically pure (IR,2R)- and (1S,2S)-1,2-bis(pentafluorophenyl)ethane- 1,2-diol (1) were synthesized from key intermediates (R)- and (S)-2-hydroxy- 2-(pentafluorophenyl)acetonitrile (2), both of which were prepared by the lipase LIP-catalyzed transesterification (E - 465). The absolute configuration of (S)-2 was determined by X-ray structural analysis after transformation into (S)-a-cyano-2,3,4,5,6-pentafluorobenzyl (S)-6-methoxy-a- methyl-2-naphthaleneacetate (S,S)-9. In addition, the crystal structure of (S,S)-9 has an interesting well-ordered packing pattern which shows face-to- face stacking interactions and end-to-end parallel contacts between the pentafluorophenyl and 6-methoxynaphthyl groups of the adjacent molecules.

Original languageEnglish
Pages (from-to)2740-2747
Number of pages8
JournalJournal of Organic Chemistry
Volume65
Issue number9
DOIs
Publication statusPublished - May 5 2000

ASJC Scopus subject areas

  • Organic Chemistry

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