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

โœ Scribed by Takashi Sakai; Yasushi Miki; Mayumi Nakatani; Tadashi Ema; Kenji Uneyama; Masanori Utaka

Book ID
104259518
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
240 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The lipase-catalyzed kinetic resolution of (+-)-2-acyloxy-2-(pentafluorophenyl)acetonitrile (+)-1 gave optically active cyanohydrin (S)-2 and its antipodal ester (R)-I (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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โœ Takashi Sakai; Tatsuo Takayama; Takafumi Ohkawa; Osamu Yoshio; Tadashi Ema; Masa ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 228 KB

A bstract: F.lficient kinetic resolution of mccmie 3-hyd~xy-3-(pentafluorophenyl)-propionittile (+)-1 by a lipa~-catalyz~l Uansesterification gave optically pure ($)-3-hyth~xy-3-(pentalluerophenyl)propionitrile (S)-I and (R)-(+)-3-aegtoxy-3-(d~nta-fluotophcnyl)Im~onitrile (R)-I [>99% ee, respectivel