6533b855fe1ef96bd12b09e6
RESEARCH PRODUCT
Acylative Dynamic Kinetic Resolution of Secondary Alcohols: Tandem Catalysis by HyperBTM and Bäckvall's Ruthenium Complex.
Ahmad Omar KhaledDavid W. PiotrowskiSimonas BalkaitisEdgars SunaArtis Kinenssubject
inorganic chemicals010405 organic chemistryArylOrganic ChemistryEnantioselective synthesischemistry.chemical_elementStereoisomerism010402 general chemistry01 natural sciencesCombinatorial chemistryCatalysisRuthenium0104 chemical sciencesRutheniumCatalysisKinetic resolutionAcylationchemistry.chemical_compoundKineticschemistryReagentAlcoholsRacemizationdescription
Non-enzymatic dynamic kinetic resolution (DKR) of secondary alcohols by enantioselective acylation using an isothiourea-derived HyperBTM catalyst and racemization of slowly reacting alcohol by Backvall's ruthenium complex is reported. The DKR approach features high enantioselectivities (up to 99:1), employs easy-to-handle crystalline 4-nitrophenyl isobutyrate as the acylating reagent, and proceeds at room temperature and under an ambient atmosphere. The stereoinduction model featuring cation-π system interactions between the acylated HyperBTM catalyst and π electrons of an alcohol aryl subunit has been elaborated by DFT calculations.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-05-11 | The Journal of organic chemistry |