ol7b02555_si_001.pdf (7.13 MB)
Stereoselective Construction of α‑Tetralone-Fused Spirooxindoles via Pd-Catalyzed Domino Carbene Migratory Insertion/Conjugate Addition Sequence
journal contribution
posted on 2017-09-21, 20:43 authored by Dhanarajan Arunprasath, Balasubramanian Devi Bala, Govindasamy SekarAn efficient diastereoselective
synthesis of α-tetralone-fused
spirooxindoles is reported. The Pd-catalyzed domino reaction proceeds
through a carbene migratory insertion followed by a 6-endo-trig mode of conjugate addition sequence from easily
accessible isatin-derived N-tosylhydrazones and 2′-iodochalcones.
The versatility of the protocol has been showcased by high functional
group tolerance, broad substrate scope, and extension to an expedient
synthesis of spiroacenaphthylenes. NMR reaction profiling and deuterium-labeling
investigations provide insight into the mechanistic pathway.
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insightSpirooxindoleiodochalconeinsertionisatin-derived Ndeuterium-labeling investigationsshowcasedsubstrate scopeTetralone-Fusedconjugate addition sequenceCarbenetosylhydrazonePd-catalyzed domino reaction proceedsPd-Catalyzed6- endoNMR reactioncarbeneα- tetralone-fused spirooxindolesspiroacenaphthylenediastereoselective synthesisversatilitygroup toleranceStereoselective ConstructionextensionMigratoryDominoSequencepathwayInsertiontrig mode
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