Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 21, Pages 6320-6324Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501273
Keywords
asymmetric synthesis; Friedel-Crafts reactions; isatin-derived ketimines; naphthols; organocatalysis
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Funding
- MINECO (Gobierno de Espana) [CTQ2013-47494-P]
- Generalitat Valenciana [ISIC2012/001]
- Universitat de Valencia
- MINECO
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A quinine-derived thiourea organocatalyst promoted the highly enantioselective addition of naphthols and activated phenols to ketimines derived from isatins. The reaction afforded chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields (up to 99%) with excellent enantioselectivity (up to 99%ee). To the best of our knowledge, this transformation is the first highly enantioselective addition of naphthols to ketimines.
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