Organocatalytic Enantioselective Aza‐Friedel–Crafts Reaction of Cyclic Ketimines with Pyrroles using Imidazolinephosphoric Acid Catalysts |
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Authors: | Prof Dr Shuichi Nakamura Nazumi Matsuda Dr Mutsuyo Ohara |
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Institution: | 1. +81)?52?735?5245;2. Frontier Research Institute for Material Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan |
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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. |
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Keywords: | aza-Friedel– Crafts reaction enantioselectivity imidazoline ketimine organocatalysis |
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