Lipase-catalyzed dynamic kinetic resolution giving optically active cyanohydrins: use of silica-supported ammonium hydroxide and porous ceramic-immobilized lipase

Takashi Sakai, Kefei Wang, Tadashi Ema

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Synthetically useful cyanohydrin acetates, ArCH(OAc)CN (Ar=C6H5, 3,4-methylenedioxyphenyl, 4-Me-C6H4, 4-Cl-C6H4, 4-F-C6H4, 4-CF3-C6H4), were successfully synthesized in high enantiomeric purities (79-93% ee) via the lipase-catalyzed dynamic kinetic resolution (DKR) of cyanohydrins synthesized in situ from the corresponding aldehydes and acetone cyanohydrin. The combined use of silica-supported BTAH (benzyltrimethylammonium hydroxide) and porous ceramic-immobilized lipase under the optimized reaction conditions enabled the remarkable acceleration of the enantioselective DKR reactions.

Original languageEnglish
Pages (from-to)2178-2183
Number of pages6
JournalTetrahedron
Volume64
Issue number9
DOIs
Publication statusPublished - Feb 25 2008

    Fingerprint

Keywords

  • Cyanohydrin
  • Dynamic kinetic resolution
  • Lipase

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this