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

T Sakai; Y Miki; M Tsuboi; H Takeuchi; T Ema; K Uneyama; M Utaka

doi:10.1021/jo9918551

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

J Org Chem. 2000 May 9;65(9):2740-7. doi: 10.1021/jo9918551.

Authors

T Sakai¹, Y Miki, M Tsuboi, H Takeuchi, T Ema, K Uneyama, M Utaka

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Okayama University, Japan.

PMID: 10808449
DOI: 10.1021/jo9918551

Abstract

Optically pure (1R,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)-alpha-cyano-2,3,4,5,6-pentafluorobenzyl (S)-6-methoxy-alpha-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.