Highly Efficient Synthesis of Enantiopure Diacetylated C2‐Symmetric Diols by Ruthenium‐ and Enzyme‐Catalyzed Dynamic Kinetic Asymmetric Transformation (DYKAT)
- 26 July 2006
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 12 (23), 6053-6061
- https://doi.org/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 ≈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.Keywords
This publication has 55 references indexed in Scilit:
- (S)‐Selective Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Secondary AlcoholsChemistry – A European Journal, 2005
- Isomerization and Deuterium Scrambling Evidence for a Change in the Rate-Limiting Step during Imine Hydrogenation by Shvo's Hydroxycyclopentadienyl Ruthenium HydrideJournal of the American Chemical Society, 2005
- Acid Zeolites as Alcohol Racemization Catalysts: Screening and Application in Biphasic Dynamic Kinetic ResolutionChemistry – A European Journal, 2004
- Highly Compatible Metal and Enzyme Catalysts for Efficient Dynamic Kinetic Resolution of Alcohols at Ambient TemperatureAngewandte Chemie, 2004
- Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient TemperatureThe Journal of Organic Chemistry, 2004
- Dynamic kinetic resolutions and asymmetric transformations by enzymes coupled with metal catalysisCurrent Opinion in Biotechnology, 2003
- Aminocyclopentadienyl Ruthenium Chloride: Catalytic Racemization and Dynamic Kinetic Resolution of Alcohols at Ambient TemperatureAngewandte Chemie International Edition, 2002
- Aminocyclopentadienyl Ruthenium Chloride: Catalytic Racemization and Dynamic Kinetic Resolution of Alcohols at Ambient TemperatureAngewandte Chemie, 2002
- Dynamic Kinetic Resolution of Secondary Diols via Coupled Ruthenium and Enzyme CatalysisThe Journal of Organic Chemistry, 1999
- Enzymatische Racematspaltung von Alkoholen gekoppelt mit Ruthenium‐katalysierter Racemisierung des Substrat‐AlkoholsAngewandte Chemie, 1997