Hydrazones as Substrates in the Synthesis of Isoxazolidines via a KOH-Promoted One-Pot Three-Component Cycloaddition with Nitroso Compounds and Olefins
Pingan Zhai, Wenhui Li, Jianying Lin, Xing Li, Wenlong Wei, Wenwen Chen
Abstract
Hydrazones have been employed as the starting materials in a KOH-mediated one-pot three-component cycloaddition with readily accessible nitroso compounds and olefins to construct various isoxazolidines. Compared with diazo compounds as starting materials, this methodology could afford a wider range of products in good to excellent yields and diastereoselectivities for most substrates, and hydrazones are cheaper, more accessible, and safer substrates. The experimental study shows that the choice of suitable hydrazones is crucial.
Topics & Concepts
CycloadditionDiazoNitrosoChemistryComponent (thermodynamics)Combinatorial chemistryOrganic chemistryCatalysisPhysicsThermodynamicsCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods