C        3-Symmetric chiral trisimidazoline-catalyzed Friedel–Crafts (FC)-type reaction

Shinobu Takizawa; Shuichi Hirata; Kenichi Murai; Hiromichi Fujioka; Hiroaki Sasai

doi:10.1039/C4OB00925H

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C₃-Symmetric chiral trisimidazoline-catalyzed Friedel–Crafts (FC)-type reaction†

Shinobu Takizawa,*^a Shuichi Hirata,^a Kenichi Murai,*^b Hiromichi Fujioka^b and Hiroaki Sasai^a

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* Corresponding authors

^a The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihoga-oka, Ibaraki-shi, Osaka 567-0047, Japan
E-mail: taki@sanken.osaka-u.ac.jp

^b Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita-shi, Osaka 565-0871, Japan
E-mail: murai@phs.osaka-u.ac.jp

Abstract

Imidazoline-catalyzed enantioselective Friedel–Crafts (FC)-type reactions were established using C₃-symmetric chiral trisimidazolines. The imidazoline catalysts promoted the FC-type reaction of aldimines with 2-naphthols to produce the corresponding adducts in high yields with up to 99% ee.

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Article information

DOI: https://doi.org/10.1039/C4OB00925H
Article type: Communication
Submitted: 06 May 2014
Accepted: 19 Jun 2014
First published: 20 Jun 2014

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Org. Biomol. Chem., 2014,12, 5827-5830

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C ₃-Symmetric chiral trisimidazoline-catalyzed Friedel–Crafts (FC)-type reaction

S. Takizawa, S. Hirata, K. Murai, H. Fujioka and H. Sasai, Org. Biomol. Chem., 2014, 12, 5827 DOI: 10.1039/C4OB00925H

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Organic & Biomolecular Chemistry