Silyl-Substituted Planar Chiral Phosphoric Acids with Ferrocene-bridged Paracyclophane Frameworks: Synthesis, Characterization, and Uses in Enantioselective aza-Friedel-Crafts Reactions - Archive ouverte HAL Access content directly
Journal Articles Advanced Synthesis and Catalysis Year : 2017

Silyl-Substituted Planar Chiral Phosphoric Acids with Ferrocene-bridged Paracyclophane Frameworks: Synthesis, Characterization, and Uses in Enantioselective aza-Friedel-Crafts Reactions

Abstract

This manuscript reports on a suitable method for the synthesis of paracyclophane type, ferrocene-bridged chiral phosphoric acids, which bear silyl-substituents on their paracyclophane frameworks. These acids have been obtained easily in enantiomerically pure form, by taking advantage of (S)-(1-phenyl-2-cyanoethyl)phosphorodiamidite as a phosphorylating agent. They have been used then as catalysts for aza-Friedel-Crafts reactions between indoles and imines, giving high catalytic activity and up to 98% enantiomeric excess.
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hal-02152293 , version 1 (11-06-2019)

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Jérémy Stemper, Kevin Isaac, Nayan Ghosh, Hortense Lauwick, Gaëtan Le duc, et al.. Silyl-Substituted Planar Chiral Phosphoric Acids with Ferrocene-bridged Paracyclophane Frameworks: Synthesis, Characterization, and Uses in Enantioselective aza-Friedel-Crafts Reactions. Advanced Synthesis and Catalysis, 2017, 359 (3), pp.519-526. ⟨10.1002/adsc.201600920⟩. ⟨hal-02152293⟩
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