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 journalArticle

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 languageEnglish
Pages (from-to)5233-5236
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number29
DOIs
Publication statusPublished - Jul 16 1998

    Fingerprint

Keywords

  • Cyanohydrins
  • Enzymes and enzyme reactions
  • Resolution
  • X-ray crystal structures

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this