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

Research output: Contribution to journalArticle

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

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Ethane
Transesterification
Lipase
Structural analysis
Crystal structure
X rays
Molecules
acetonitrile

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Lipase-catalyzed transesterification of 2-hydroxy-2- (pentafluorophenyl)acetonitrile leading to (1R,2R)-and (1S,2S)-bis (pentafluorophenyl)ethane-1,2-diol. / Sakai, Takashi; Miki, Yasushi; Tsuboi, Masashi; Takeuchi, Hiroaki; Ema, Tadashi; Uneyama, Kenji; Utaka, Masanori.

In: Journal of Organic Chemistry, Vol. 65, No. 9, 05.05.2000, p. 2740-2747.

Research output: Contribution to journalArticle

Sakai, Takashi ; Miki, Yasushi ; Tsuboi, Masashi ; Takeuchi, Hiroaki ; Ema, Tadashi ; Uneyama, Kenji ; Utaka, Masanori. / Lipase-catalyzed transesterification of 2-hydroxy-2- (pentafluorophenyl)acetonitrile leading to (1R,2R)-and (1S,2S)-bis (pentafluorophenyl)ethane-1,2-diol. In: Journal of Organic Chemistry. 2000 ; Vol. 65, No. 9. pp. 2740-2747.
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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.",
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AU - Sakai, Takashi

AU - Miki, Yasushi

AU - Tsuboi, Masashi

AU - Takeuchi, Hiroaki

AU - Ema, Tadashi

AU - Uneyama, Kenji

AU - Utaka, Masanori

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N2 - 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.

AB - 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.

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