Diastereo- and Enantioselective Chemodivergent Three-Component Cascade Reactions via Gold and Carbene Sequential Catalysis
Shulei Zhang, Shaojie Wang, Xiaolan Xin, Xia Wang, Zhifeng Tu, Shenci Lu
Abstract
This study investigates the feasibility and inherent benefits of combining transition-metal- and organoasymmetric-catalyzed reactions in one pot. The reported transformation features Au-catalyzed tandem hydration–oxacyclization and NHC-catalyzed enantioselective annulation, effectively converting simple skipped diynones, water, and enals into highly diastereo- and enantioenriched fused heterocycles. Furthermore, the chemoselectivity controlled by the base is particularly noteworthy, enabling facile access to ε-lactones or spiro heterocycles from the same set of starting materials.
Topics & Concepts
CarbeneEnantioselective synthesisCatalysisCascadeComponent (thermodynamics)ChemistryCombinatorial chemistryCascade reactionOrganic chemistryPhysicsChromatographyThermodynamicsCatalytic Alkyne ReactionsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCyclopropane Reaction Mechanisms