Enantioselective Mannich reaction between rhodanines and isatin-derived ketimines to construct vicinal tetrasubstituted stereocenters

An organocatalytic enantioselective Mannich reaction between rhodanines and isatin-derived ketimines was developed. With 2 mol% of a quinine-based tertiary amine-thiourea catalyst C2, 3,3-disubstituted oxindoles with vicinal tetrasubstituted stereocenters were obtained in moderate-to-excellent yield...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (32), p.5780-5787
Main Authors: Xu, Han, Kang, Tian-Chen, Sha, Feng, Wu, Xin-Yan
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Enantiomers
Imines
Quinine
Stereoselectivity
Substrates
Thiourea
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Summary:An organocatalytic enantioselective Mannich reaction between rhodanines and isatin-derived ketimines was developed. With 2 mol% of a quinine-based tertiary amine-thiourea catalyst C2, 3,3-disubstituted oxindoles with vicinal tetrasubstituted stereocenters were obtained in moderate-to-excellent yields (43-99%) with excellent diastereoselectivities (98 : 2-99 : 1 dr) and good-to-excellent enantioselectivities (up to 97% ee). The readily available substrates, low catalyst loading and high stereoselectivity are the major features.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01524d