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Synfacts 2014; 10(5): 0487
DOI: 10.1055/s-0033-1341177
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Friedel–Crafts Reaction Using a Chiral-at-Metal Iridium Catalyst

Contributor(s):
Mark Lautens
,
David A. Petrone
Huo H, Fu C, Harms K, Meggers E * Philipps-Universität Marburg, Germany and Xiamen University, P. R. of China
Asymmetric Catalysis with Substitutionally Labile yet Stereochemically Stable Chiral-at-Metal Iridium(III) Complex.

J. Am. Chem. Soc. 2014;
136: 2990-2993
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Publication History

Publication Date:
17 April 2014 (online)

 
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Key words

chiral-at-metal iridium complexes - imidazoles - indoles

Significance

The widespread use of asymmetric catalysis in academia and industry can be directly attributed to the vast array of synthetically and commercially available chiral ligands. However, the utilization of chiral-at-metal complexes in asymmetric catalysis is relatively underdeveloped. Here, the authors report the efficient synthesis of a chiral-at-iridium catalyst and its application to an asymmetric Friedel–Crafts reaction.


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Comment

The authors present the asymmetric Friedel–Crafts reaction of indoles and acyl imida­zole derivatives using a chiral-at-iridium complex as catalyst. The reaction proceeds with excellent yields and selectivities by employing a low loading (1–2 mol%) of this interesting catalyst. The authors suggest that once coordinated, the achiral ligands block the re face of the indole, resulting in a highly selective si-face attack.


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