Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles

Xavier Companyó, Guillem Valero, Oriol Pineda, Teresa Calvet, Mercè Font-Bardía, Albert Moyano, Ramon Rios

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

An enantioselective α-oxyamination of unprotected 3-substituted oxindoles with nitrosobenzene catalyzed by tertiary amine-thiourea bifunctional organocatalysts has been developed and affords the corresponding 3-amino-2-oxindole derivatives in good yields and with moderate to excellent enantioselectivities (up to > 99.9:0.1 er when the product is isolated by direct filtration from the reaction mixture). The absolute configuration of the major enantiomers of the products has been established both by chemical correlation and by comparison between the theoretically calculated and the experimental ECD.

Original languageBritish English
Pages (from-to)431-439
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number2
DOIs
StatePublished - 14 Jan 2012

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