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RESEARCH PRODUCT
Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution
Savannah C. ZachariasAnton AxelssonMatti HaukkaAugust RunemarkHenrik SundénHenrik SundénMathias Westerlundsubject
ChemistryOrganocatalysisOrganic ChemistryEnantioselective synthesisSingle stepPhysical and Theoretical ChemistrySelectivityCombinatorial chemistryCatalysisKinetic resolutionStereocenterdescription
An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, with good-to-moderate yields. Mechanistic studies indicate that the rate-determining step of the reaction is the formation of the Breslow intermediate, while the selectivity determining step occurs later in the mechanism. The presented methodology enables rapid synthesis of complex structures in a single step.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-07-06 | European Journal of Organic Chemistry |