6533b86efe1ef96bd12cb468
RESEARCH PRODUCT
Switchable Access to Different Spirocyclopentane Oxindoles by N-Heterocyclic Carbene Catalyzed Reactions of Isatin-Derived Enals and N-Sulfonyl Ketimines
Marcus BlümelLei WangLei WangSun LiKari RissanenAnssi PeuronenDieter EndersRakesh Puttreddysubject
Annulationasymmetric synthesis010402 general chemistry01 natural sciencesCatalysisStereocenterchemistry.chemical_compoundkatalyytitMoietyOrganic chemistryorganocatalysisN-heterocyclic carbenesheterosykliset yhdisteetspiro-compoundsta116Sulfonylchemistry.chemical_classificationkemiallinen synteesiheterocycles010405 organic chemistryIsatinEnantioselective synthesisGeneral ChemistryGeneral Medicine0104 chemical scienceschemistryOrganocatalysisCarbenedescription
A novel NHC-catalyzed annulation protocol for the asymmetric synthesis of biologically important β-lactam fused spirocyclopentane oxindoles with four contiguous stereocenters, including two quaternary carbon centers, was developed. Alternatively, spirocyclopentane oxindoles containing an enaminone moiety can be achieved using the same starting materials, isatin-derived enals, and N-sulfonyl ketimines, in the presence of a slightly different NHC catalytic system. This switchable annulation strategy enables the selective assembly of both heterocyclic scaffolds with good yields and excellent enantioselectivities for a broad range of substrates.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-06-20 | Angewandte Chemie |