Akiyama-Terada Catalyst

Akiyama-Terada Catalyst

  • General Characteristics

The phosphoric acids containing an appropriately substituted BINOL backbone function as chiral Brønsted acid catalysts that can promote a wide range of stereoselective reactions.

Reported independently in 2004 by the laboratories of Takahiko Akimaya (of Gakushuin University, Japan) and Masahiro Terada (Tohoku University, Japan), these catalysts are called the Akiyama-Terada catalysts.

A number of modified catalysts have been reported more recently, including the imide version and the chiral counter anion version. The versatility of these catalysts makes them one of the most popular organocatalyst classes known today.

  • General References

  • Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566. DOI: 10.1002/anie.200353240
  • Uraguchi, D.; Terada, M. J. Am. Chem. Soc.2004, 126, 5365. DOI: 10.1021/ja0491533


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  • Reaction Mechanism

  • Examples

The phosphoric acid-catalyzed reactions are by no means limited to additions to imines. An example shown below is the asymmetric Nazarov cyclization.[1]


In the asymmetric α-allylation of aldehydes via π-allylpalladium, the phosphoric acid and the palladium can coexist and cooperate to achieve the synthesis of all-carbon quaternary stereogenic centers in high enantioselectivity.[2] terada_akiyama_2.gif

An example in which the phosphoric acid was used as the counter anion of a gold catalyst.[3] This concept is helpful when neutral chiral ligands are ineffective in creating the chiral environment.


  • Experimental Procedure

  • Experimental Tips

  • References

[1] Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J. Angew. Chem. Int. Ed. 2007, 46,
2097. DOI: 10.1002/anie.200604809 [2] Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336. DOI: 10.1021/ja074678r [3] Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496. DOI:10.1126/science.1145229

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  • External Links

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