Asymmetric Catalytic Diverse Ring Opening/Cycloadditions of Cyclobutenones with (<i>E</i>)-Alkenyloxindoles and (<i>E</i>)-Dioxopyrrolidines
Yao Luo, Hang Zhang, Siyuan Wang, Yuqiao Zhou, Shunxi Dong, Xiaoming Feng
Abstract
Highly enantioselective ring-opening/cycloaddition reactions of cyclobutenones were achieved by employing chiral N,N′-dioxide/metal complexes as the catalysts. The Diels–Alder type cycloaddition with (E)-alkenyloxindoles yielded spirocyclohexaneoxindoles with excellent results. Meanwhile, a hetero-Diels–Alder process occurred with (E)-dioxopyrrolidines to afford spiropyrrolidinone-dihydropyranone derivatives.
Topics & Concepts
CycloadditionChemistryEnantioselective synthesisCatalysisRing (chemistry)StereochemistryMedicinal chemistryOrganic chemistryAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms