A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
Switchable Access to Different Spirocyclopentane Oxindoles by N-Heterocyclic Carbene Catalyzed Reactions of Isatin-Derived Enals and N-Sulfonyl Ketimines
Tekijät: Wang L, Li S, Blumel M, Puttreddy R, Peuronen A, Rissanen K, Enders D
Kustantaja: WILEY-V C H VERLAG GMBH
Julkaisuvuosi: 2017
Journal: Angewandte Chemie International Edition
Tietokannassa oleva lehden nimi: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Lehden akronyymi: ANGEW CHEM INT EDIT
Vuosikerta: 56
Numero: 29
Aloitussivu: 8516
Lopetussivu: 8521
Sivujen määrä: 6
ISSN: 1433-7851
DOI: https://doi.org/10.1002/anie.201704210
Tiivistelmä
A novel NHC-catalyzed annulation protocol for the asymmetric synthesis of biologically important beta-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.
A novel NHC-catalyzed annulation protocol for the asymmetric synthesis of biologically important beta-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.
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