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Organocatalytic Asymmetric Addition of Naphthols and Electron‐Rich Phenols to Isatin‐Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters |
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| Authors: | Marc Montesinos‐Magraner Dr Carlos Vila Rubén Cantón Prof?Dr Gonzalo Blay Dr Isabel Fernández Prof?Dr M Carmen Muñoz Prof?Dr José R Pedro |
| Institution: | 1. Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València (Spain);2. Departament de Física Aplicada, Universitat Politècnica de València, Camino de Vera s/n, 46022 València (Spain) |
| 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: | asymmetric synthesis Friedel– Crafts reactions isatin‐derived ketimines naphthols organocatalysis |