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. 2015 May 18;54(21):6320-4.
doi: 10.1002/anie.201501273. Epub 2015 Apr 2.

Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: highly enantioselective construction of tetrasubstituted stereocenters

Marc Montesinos-Magraner  1 , Carlos Vila  1 , Rubén Cantón  1 , Gonzalo Blay  1 , Isabel Fernández  1 , M Carmen Muñoz  2 , José R Pedro  3
Affiliations

Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: highly enantioselective construction of tetrasubstituted stereocenters

Marc Montesinos-Magraner et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: Friedel-Crafts reactions; asymmetric synthesis; isatin-derived ketimines; naphthols; organocatalysis.

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