Efficient Entry to Diversely Functionalized Spirocyclic Oxindoles from Isatins through Carbonyl-Addition/Cyclization Reaction Sequences

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 α-allenols have been o...

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Veröffentlicht in:	Journal of organic chemistry 2006-03, Vol.71 (6), p.2346-2351
Hauptverfasser:	Alcaide, Benito, Almendros, Pedro, Rodríguez-Acebes, Raquel
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	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 α-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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0525027