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

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...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2018-11, Vol.5 (22), p.3226-3230
Main Authors: Huang, Qiuhong, Cheng, Yuyu, Yuan, Huijun, Chang, Xiaoyong, Li, Pengfei, Li, Wenjun
Format: Article
Language:English
Subjects:
Crystallography
Enantiomers
Imines
Organic chemistry
Phosphoric acid
Substitutes
Sulfur
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/c8qo00814k