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 › peer-review

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

Keywords

Cyanohydrins
Enzymes and enzyme reactions
Resolution
X-ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Lipase-catalyzed kinetic resolution of 2-acyloxy-2- (pentafluorophenyl)acetonitrile",

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.",

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T1 - Lipase-catalyzed kinetic resolution of 2-acyloxy-2- (pentafluorophenyl)acetonitrile

AU - Sakai, Takashi

AU - Miki, Yasushi

AU - Nakatani, Mayumi

AU - Ema, Tadashi

AU - Uneyama, Kenji

AU - Utaka, Masanori

PY - 1998/7/16

Y1 - 1998/7/16

N2 - 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.

AB - 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.

KW - Cyanohydrins

KW - Enzymes and enzyme reactions

KW - Resolution

KW - X-ray crystal structures

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