Recursive Anion-Triggered Tandem Reactions of <i>ortho</i>-Bis-ynones: Tunable Synthesis of 1-Indenones and Cyclopenta[<i>a</i>]inden-8(2<i>H</i>)-ones
Anilkumar Gunnam, Alagesan Balasubramani, Goverdhan Mehta
Abstract
Recursive anion-mediated activation of o-bis-ynones sets off a Michael addition–aldol reaction–dehydrative rearrangement cascade, leading to the one-pot synthesis of 1-indenones via orthogonal interplay between the two ortho-ynone moieties. Repeating the recursive anion engagement with the 1-indenones unfolded access to a functionally embellished cyclopenta[a]inden-8(2H)-one core and its spiroannulated analogues either directly or stepwise through tandem 1,6-Michael-type addition–6π electrocyclization and an in situ oxidation sequence.
Topics & Concepts
TandemChemistryAldol reactionCascade reactionSequence (biology)CascadeStereochemistryCombinatorial chemistryIonMedicinal chemistryOrganic chemistryCatalysisMaterials scienceBiochemistryChromatographyComposite materialCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis