Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 15, Pages 3645-3655Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900414
Keywords
Asymmetric catalysis; 3-Aminooxindoles; Chiral pyrazoles; Bifunctional thioureas; Mannich reaction; Supported thioureas
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Funding
- Spanish MINECO [FEDER-CTQ 2014-59870-P]
- Junta de Castilla y Leon [FEDER-VA115P17, VA149G18]
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Enantioenriched 3-amino-3-substituted oxindoles have been obtained by addition of different nucleophiles to N-Boc ketimines derived from isatin catalyzed by chiral bifunctional supported thioureas. The Mannich reaction occurs with excellent enantioselection, but poor diastereoselection when prochiral nucleophiles were used. The supported catalyst were recovered and reused for five times without loss of activity. The mixture of diastereoisomers formed when a prochiral structure was used as nucleophile was converted into a single enantioenriched pyrazolyl derivative.
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