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DOI: 10.1055/s-0033-1341177
Asymmetric Friedel–Crafts Reaction Using a Chiral-at-Metal Iridium Catalyst
Publikationsverlauf
Publikationsdatum:
17. April 2014 (online)
![](https://www.thieme-connect.de/media/synfacts/201405/i_l035_s1_10-1055_s-0033-1341177.gif)
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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![](https://www.thieme-connect.de/media/synfacts/201405/i_l035_s1_10-1055_s-0033-1341177.gif)