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

MontesinosMagraner Marc | Zendy; Vila Carlos | Zendy; Cantón Rubén | Zendy; Blay Gonzalo | Zendy; Fernández Isabel | Zendy; Muñoz M. Carmen | Zendy; Pedro José R. | Zendy

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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 international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201501273

Subject(s) - enantioselective synthesis , stereocenter , isatin , chemistry , organocatalysis , thiourea , phenols , cinchona , organic chemistry , 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.

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