Lipase-catalyzed efficient kinetic resolution of 3-Hydroxy-3-(pentafluorophenyl)propionitrile

Takashi Sakal; Tetsuo Takayama; Takafumi Ohkawa; Osamu Yoshio; Tadashi Ema; Masanori Utaka

doi:10.1016/S0040-4039(97)00255-4

Lipase-catalyzed efficient kinetic resolution of 3-Hydroxy-3-(pentafluorophenyl)propionitrile

Takashi Sakal, Tetsuo Takayama, Takafumi Ohkawa, Osamu Yoshio, Tadashi Ema, Masanori Utaka

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

Efficient kinetic resolution of racemic 3-hydroxy-3-(pentafluorophenyl)- propionitrile (±)-1 by a lipase-catalyzed transesterification gave optically pure (S)-3-hydroxy-3-(pentafluorophenyl-)propionitrile (S)-1 and (R)-(+)-3-acetoxy-3-(penta-fluorophenyl)propionitrile (R)-1 [>99% ee, respectively, E = 1057], the former of which was further transformed into (S)-(-)-3-amino-1-(pentafluorophenyl)-1-propanol (S)-7 in four steps.

Original language	English
Pages (from-to)	1987-1990
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(97)00255-4
Publication status	Published - Mar 17 1997

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Lipase-catalyzed efficient kinetic resolution of 3-Hydroxy-3-(pentafluorophenyl)propionitrile",

abstract = "Efficient kinetic resolution of racemic 3-hydroxy-3-(pentafluorophenyl)- propionitrile (±)-1 by a lipase-catalyzed transesterification gave optically pure (S)-3-hydroxy-3-(pentafluorophenyl-)propionitrile (S)-1 and (R)-(+)-3-acetoxy-3-(penta-fluorophenyl)propionitrile (R)-1 [>99% ee, respectively, E = 1057], the former of which was further transformed into (S)-(-)-3-amino-1-(pentafluorophenyl)-1-propanol (S)-7 in four steps.",

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T1 - Lipase-catalyzed efficient kinetic resolution of 3-Hydroxy-3-(pentafluorophenyl)propionitrile

AU - Sakal, Takashi

AU - Takayama, Tetsuo

AU - Ohkawa, Takafumi

AU - Yoshio, Osamu

AU - Ema, Tadashi

AU - Utaka, Masanori

PY - 1997/3/17

Y1 - 1997/3/17

N2 - Efficient kinetic resolution of racemic 3-hydroxy-3-(pentafluorophenyl)- propionitrile (±)-1 by a lipase-catalyzed transesterification gave optically pure (S)-3-hydroxy-3-(pentafluorophenyl-)propionitrile (S)-1 and (R)-(+)-3-acetoxy-3-(penta-fluorophenyl)propionitrile (R)-1 [>99% ee, respectively, E = 1057], the former of which was further transformed into (S)-(-)-3-amino-1-(pentafluorophenyl)-1-propanol (S)-7 in four steps.

AB - Efficient kinetic resolution of racemic 3-hydroxy-3-(pentafluorophenyl)- propionitrile (±)-1 by a lipase-catalyzed transesterification gave optically pure (S)-3-hydroxy-3-(pentafluorophenyl-)propionitrile (S)-1 and (R)-(+)-3-acetoxy-3-(penta-fluorophenyl)propionitrile (R)-1 [>99% ee, respectively, E = 1057], the former of which was further transformed into (S)-(-)-3-amino-1-(pentafluorophenyl)-1-propanol (S)-7 in four steps.

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