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Organocatalytic Asymmetric Addition of Naphthols and Electron‐Rich Phenols to Isatin‐Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters
Author(s) -
MontesinosMagraner Marc,
Vila Carlos,
Cantón Rubén,
Blay Gonzalo,
Fernández Isabel,
Muñoz M. Carmen,
Pedro José R.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501273
Subject(s) - enantioselective synthesis , stereocenter , chemistry , isatin , organocatalysis , thiourea , organic chemistry , phenols , cinchona , catalysis
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.