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Organocatalytic enantioselective Mannich-type addition of 5H-thiazol-4-ones to isatin-derived imines: access to 3-substituted 3-amino-2-oxindoles featured by vicinal sulfur-containing tetrasubstituted stereocenters

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Abstract

The first chiral phosphoric acid catalyzed enantioselective nucleophilic addition of 5H-thiazol-4-ones to isatin-derived imines has been established. By using this strategy, the resulting 3-substituted 3-amino-2-oxindoles featuring both 5H-thiazol-4-one and vicinal sulfur-containing tetrasubstituted stereocenter structural motifs were obtained in high yields with excellent enantioselectivities and diastereoselectivities.

Graphical abstract: Organocatalytic enantioselective Mannich-type addition of 5H-thiazol-4-ones to isatin-derived imines: access to 3-substituted 3-amino-2-oxindoles featured by vicinal sulfur-containing tetrasubstituted stereocenters

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Publication details

The article was received on 02 Aug 2018, accepted on 27 Sep 2018 and first published on 28 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00814K
Citation: Org. Chem. Front., 2018, Advance Article
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    Organocatalytic enantioselective Mannich-type addition of 5H-thiazol-4-ones to isatin-derived imines: access to 3-substituted 3-amino-2-oxindoles featured by vicinal sulfur-containing tetrasubstituted stereocenters

    Q. Huang, Y. Cheng, H. Yuan, X. Chang, P. Li and W. Li, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00814K

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