Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-05, Vol.54 (21), p.6320-6324
Main Authors: Montesinos-Magraner, Marc, Vila, Carlos, Cantón, Rubén, Blay, Gonzalo, Fernández, Isabel, Muñoz, M. Carmen, Pedro, José R.
Format: Article
Language:English
Subjects:
Activated
asymmetric synthesis
Asymmetry
Construction
Friedel-Crafts reactions
isatin-derived ketimines
Naphthol
naphthols
organocatalysis
Phenols
Thioureas
Transformations
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Summary: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. Gentle persuasion: A quinine‐derived thiourea organocatalyst was found to promote the asymmetric addition of naphthols and activated phenols to ketimines derived from isatins (see scheme; Boc=tert‐butoxycarbonyl). The reaction under mild conditions afforded chiral 3‐amino‐2‐oxindoles containing a quaternary stereocenter in high yields (up to 99 %) with excellent enantioselectivity (up to 99 % ee).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201501273