Highly efficient synthesis of enantiopure diacetylated C(2)-symmetric diols by ruthenium- and enzyme-catalyzed dynamic kinetic asymmetric transformation (DYKAT)

Chemistry. 2006 Aug 7;12(23):6053-61. doi: 10.1002/chem.200600257.

Abstract

Highly efficient synthesis of enantiopure diacetates of 2,4-pentanediol and 2,5-hexanediol starting from commercially available mixtures of the diols (dl/meso approximately 1:1) has been realized by combining a fast ruthenium-catalyzed epimerization with an enzymatic transesterification. The in situ coupling of these two processes produces the diacetates in high yield in >99 % enantiomeric excess.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Catalysis
  • Glycols / chemical synthesis*
  • Glycols / chemistry
  • Kinetics
  • Lipase / chemistry*
  • Molecular Conformation
  • Organometallic Compounds / chemistry*
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Glycols
  • Organometallic Compounds
  • 2,5-hexanediol
  • 2,4-pentanediol
  • Ruthenium
  • Lipase