Lipase-catalyzed kinetic resolution of 2-acyloxy-2- (pentafluorophenyl)acetonitrile

Takashi Sakai; Yasushi Miki; Mayumi Nakatani; Tadashi Ema; Kenji Uneyama; Masanori Utaka

doi:10.1016/S0040-4039(98)01029-6

Lipase-catalyzed kinetic resolution of 2-acyloxy-2- (pentafluorophenyl)acetonitrile

Takashi Sakai, Yasushi Miki, Mayumi Nakatani, Tadashi Ema, Kenji Uneyama, Masanori Utaka

Research output: Contribution to journal › Article

26 Citations (Scopus)

Abstract

The lipase-catalyzed kinetic resolution of (±)-2-acyloxy-2- (pentafluorophenyl)acetonitrile (±)-1 gave optically active cyanohydrin (S)- 2 and its antipodal ester (R)-1 (E = 211), the former of which was transformed (TBSOTf, DMAP) into its TBS-ether (S)-3, a new fluorinated chiral building block, and into naproxen ester 4 for X-ray analysis to determine the absolute configuration.

Original language	English
Pages (from-to)	5233-5236
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4039(98)01029-6
Publication status	Published - Jul 16 1998

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Keywords

Cyanohydrins
Enzymes and enzyme reactions
Resolution
X-ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Sakai, T., Miki, Y., Nakatani, M., Ema, T., Uneyama, K., & Utaka, M. (1998). Lipase-catalyzed kinetic resolution of 2-acyloxy-2- (pentafluorophenyl)acetonitrile. Tetrahedron Letters, 39(29), 5233-5236. https://doi.org/10.1016/S0040-4039(98)01029-6

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AU - Uneyama, Kenji

AU - Utaka, Masanori

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KW - X-ray crystal structures

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10.1016/S0040-4039(98)01029-6