Stereoselective Construction of α‑Tetralone-Fused
Spirooxindoles via Pd-Catalyzed Domino Carbene Migratory Insertion/Conjugate
Addition Sequence
Posted on 2017-09-21 - 20:43
An 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.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Arunprasath, Dhanarajan; Devi Bala, Balasubramanian; Sekar, Govindasamy (2017). Stereoselective Construction of α‑Tetralone-Fused
Spirooxindoles via Pd-Catalyzed Domino Carbene Migratory Insertion/Conjugate
Addition Sequence. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02555
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
AUTHORS (3)
DA
Dhanarajan Arunprasath
BD
Balasubramanian Devi Bala
GS
Govindasamy Sekar
KEYWORDS
insightSpirooxindoleiodochalconeinsertionisatin-derived Ndeuterium-labeling investigationsshowcasedsubstrate scopeTetralone-Fusedconjugate addition sequenceCarbenetosylhydrazonePd-catalyzed domino reaction proceedsPd-Catalyzed6- endoNMR reactioncarbeneα- tetralone-fused spirooxindolesspiroacenaphthylenediastereoselective synthesisversatilitygroup toleranceStereoselective ConstructionextensionMigratoryDominoSequencepathwayInsertiontrig mode