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Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles

Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles
Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles
An enantioselective ?-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.
1477-0520
431-439
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Pineda, Oriol
242d1bb9-4be7-4fc2-a3ba-2db1e98dec1d
Calvet, Teresa
07d81814-6e36-4aa0-9f28-db0c7e3b1849
Font-Bardía, Mercè
2526234d-9a51-4fe2-bf43-537db1ca5dac
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Pineda, Oriol
242d1bb9-4be7-4fc2-a3ba-2db1e98dec1d
Calvet, Teresa
07d81814-6e36-4aa0-9f28-db0c7e3b1849
Font-Bardía, Mercè
2526234d-9a51-4fe2-bf43-537db1ca5dac
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Companyó, Xavier, Valero, Guillem, Pineda, Oriol, Calvet, Teresa, Font-Bardía, Mercè, Moyano, Albert and Rios, Ramon (2012) Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles. Organic & Biomolecular Chemistry, 10 (2), 431-439. (doi:10.1039/C1OB06503C). (PMID:22113541)

Record type: Article

Abstract

An enantioselective ?-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.

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e-pub ahead of print date: 6 October 2011
Published date: 2012
Organisations: Chemistry

Identifiers

Local EPrints ID: 347684
URI: http://eprints.soton.ac.uk/id/eprint/347684
ISSN: 1477-0520
PURE UUID: ba264e80-3721-45da-b72c-211b0d53339e
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 10:04
Last modified: 03 Dec 2019 01:38

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