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Organocatalytic Enantioselective Aza‐Friedel–Crafts Reaction of Cyclic Ketimines with Pyrroles using Imidazolinephosphoric Acid Catalysts
Authors:Prof Dr Shuichi Nakamura  Nazumi Matsuda  Dr Mutsuyo Ohara
Institution:1. +81)?52?735?5245;2. Frontier Research Institute for Material Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan
Abstract:Organocatalytic enantioselective aza‐Friedel–Crafts reactions of cyclic ketimines with pyrroles or indoles were catalyzed by imidazoline/phosphoric acid catalysts. The reaction was applied to various 3H‐indol‐3‐ones to afford products in excellent yields and enantioselectivities. The chiral catalysts can be recovered by a single separation step using column chromatography and are reusable without further purification. Based on the experimental investigations, a possible transition state has been proposed to explain the origin of the asymmetric induction.
Keywords:aza-Friedel–  Crafts reaction  enantioselectivity  imidazoline  ketimine  organocatalysis
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