The Department of Organic Chemistry kindly invites to a guest lecture by Prof. Takahiko Akiyama, Department of Chemistry, Gakushuin University, Tokyo, Japan:

Title: “Recent Progress in the Chiral Phosphoric Acid Catalysis”

Abstract:

Development of efficient chiral catalysts continues to be one of the most important challenge in
synthetic organic chemistry. We already reported that chiral phosphoric acid 1, derived from (R)-
BINOL, functioned as a bifunctional chiral Brønsted acid catalyst for a number of enantioselective
reactions.¹
We will discuss recent progress on the chiral phosphoric acid catalysis, such as Friedel-Crafts alkylation reaction of indole with nitroalkenes (Scheme 1),² Friedel-Crafts alkylation reaction of pyrrole with CF3-substituted N-H ketimines (Scheme 2),³ radical addition to aldimines (Scheme 3),⁴ and palladium (II) phosphate catalyzed desymmetrization of biaryl compounds by C(sp³)−H activation.

References

1. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566-1568. Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2007, 129, 6756-6764. Akiyama, T. Chem. Rev. 2007, 107, 5744-5758.
2. Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem. Int. Ed. 2008, 47, 4016-4018. Mori, K.; Wakazawa, M.; Akiyama, T. Chem. Sci. 2014, 5, 1799-1803. Ibáñez, I.; Kaneko, M.; Kamei, Y.; Tsutsumi, R.; Yamanaka, M.; Akiyama, T. ACS Catal. 2019, 9, 6903-6909. Uchikura, T.; Yokohama, S.; Murakami, M.; Akiyama, T. Synthesis 2022, 54, 3793-3800.
3. Miyagawa, M.; Yoshida, M.; Kiyota, Y.; Akiyama, T. Chem. Eur. J. 2019, 25, 5677-5681. Uchikura, T.; Suzuki, R.; Suda, Y.; Akiyama, T. ChemCatChem 2020, 12, 4784-4787. Uchikura, T.; Aruga, K.; Suzuki, R.; Akiyama, T. Org. Lett. 2022, 24, 4699–4703.
4. Uchikura, T.; Kamiyama, N.; Mouri, T.; Akiyama, T. ACS Catal. 2022, 12, 5209–5216.
5. Uchikura, T.; Kato, S.; Makino, Y.; Fujikawa, M. J.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2023, 145, 15906–15911.