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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization
Benito Alcaide1, Pedro Almendros, Raquel Rodríguez-Acebes
1Departamento de Química Organica I, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain. alcaideb@quim.ucm.es
Abstract:
A novel approach to diversely functionalized spirocyclic oxindoles has been developed by using different metal-mediated carbonyl-addition/cyclization reaction sequences. Spirocyclization precursors, 2-indolinone-tethered homoallylic alcohols, (buta-1,3-dien-2-yl)methanols, and alpha-allenols have been obtained by regioselective addition of stabilized organoindium reagents to isatins in aqueous environment. Ruthenium-, silver-, and palladium-catalyzed reactions of the above unsaturated alcohol derivatives provided oxaspiro oxindoles.
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