6533b86cfe1ef96bd12c8a9d
RESEARCH PRODUCT
Ionic liquids as precatalysts in the highly stereoselective conjugate addition of α,β-unsaturated aldehydes to chalcones.
Anton AxelssonJoachim BijlLinda TaHenrik SundénMatti Haukkasubject
Green chemistryChemistryOrganic ChemistryGeneral ChemistryCatalysischemistry.chemical_compoundIonic liquidMoietyOrganic chemistryReactivity (chemistry)StereoselectivitySelectivityta116Conjugatedescription
Imidazolium-based ionic liquids (ILs) serve both as recyclable reaction media and as precatalysts for the N-heterocyclic carbene-catalyzed conjugate addition of α,β-unsaturated aldehydes to chalcones. The reaction produces a broad scope of 1,6-ketoesters incorporating an anti-diphenyl moiety in high yields and with high stereoselectivity. In recycling experiments, the IL can be reused up to five times with retained reactivity and selectivity. Moreover, the 1,6-ketoesters form self-assembled organogels in aliphatic hydrocarbons. The reaction protocol is robust, easily operated, scalable and highly functionalized compounds can be obtained from inexpensive and readily accessible starting materials.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-07-08 | Chemistry (Weinheim an der Bergstrasse, Germany) |