Assembly of Spirooxindole Derivatives via Organocatalytic Iminium-Enamine Cascade Reactions

The assembly of complex spirocyclopentaneoxindoles via a novel organocatalytic iminium-enamine cascade process is reported. Reactions between 3-substituted oxindoles and α,β-unsaturated aldehydes catalyzed by second generation prolinol ethers provided the desired products in high yield with excellen...

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Veröffentlicht in:	Organic letters 2012-12, Vol.14 (23), p.5968-5971
Hauptverfasser:	Albertshofer, Klaus, Anderson, Kimberly E, Barbas, Carlos F
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Catalysis Combinatorial Chemistry Techniques Ethers - chemistry Heterocyclic Compounds, 3-Ring - chemical synthesis Heterocyclic Compounds, 3-Ring - chemistry Indoles - chemistry Molecular Structure Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	The assembly of complex spirocyclopentaneoxindoles via a novel organocatalytic iminium-enamine cascade process is reported. Reactions between 3-substituted oxindoles and α,β-unsaturated aldehydes catalyzed by second generation prolinol ethers provided the desired products in high yield with excellent levels of enantioselectivity in a single step.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol302876c