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
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- PMID: 25845341
- DOI: 10.1002/anie.201501273
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Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: highly enantioselective construction of tetrasubstituted stereocenters
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.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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