A copper-catalyzed three-component reaction of dithioacetals with diazo ketones and ketimines

Zinc(II)-catalyzed [2+2+1] annulation of internal alkenes, diazooxindoles, and isocyanates was successfully developed for the construction of multisubstituted spirooxindoles. This multicomponent transformation involves in situ generation of a sulfurcontaining spirocyclic intermediate from the [4+1] annulation of diazooxindole to sulfonyl isocyanate, which subsequently reacts as a 1,3-dipole with the internal alkene, that is, α-oxo ketene dithioacetal, to furnish a formal [2+2+1] annulation in a one-pot manner. This synthetic protocol features a low-toxicity main group metal catalyst, readily available reagents, and ≤96% yields, offering an efficient route to multisubstituted spirooxindole derivatives.

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Zinc(II)-Catalyzed [2+2+1] Annulation of Internal Alkenes, Diazooxindoles, and Isocyanates to Access Spirooxindoles

Huang

Lin

et al. 2023

Org. Lett.

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A copper-catalyzed three-component reaction of dithioacetals with diazo ketones and ketimines

Abstract: A copper-catalyzed three-component reaction of dithioacetals with diazo-ketones and ketimines has been reported. This reaction proceeds via trapping of the highly active sulfur ylide species, which generated from thioacetal and...

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Zinc(II)-Catalyzed [2+2+1] Annulation of Internal Alkenes, Diazooxindoles, and Isocyanates to Access Spirooxindoles

Zinc(II)-Catalyzed [2+2+1] Annulation of Internal Alkenes, Diazooxindoles, and Isocyanates to Access Spirooxindoles

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