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Synthesis of Chiral 1,1-Binaphthyl 2,2-Disulfonic Acids (BINSAs) toward Asymmetric Catalysis

  • School of Engineering/Graduate School of Engineering
  • Department of Molecular and Macromolecular Chemistry
  • Research Group of Molecular Chemistry
  • (Laboratory of Catalysis in Organic Synthesis)

Kazuaki Ishihara [Professor]

http://www.ishihara-lab.net/english/

  • School of Engineering/Graduate School of Engineering
  • Department of Molecular and Macromolecular Chemistry
  • Research Group of Molecular Chemistry
  • (Laboratory of Catalysis in Organic Synthesis)

Manabu Hatano [Associate Professor]

Outline of Seeds

We developed the efficient synthesis of chiral BINSAs. Chiral BINSA acts as not only as an organocatalyst, but also as a chiral ligand for metal species. In particular, we developed chiral BINSA ammonium salts as acidbase combined catalysts which can be tailor-made for each substrate and/or reagent in catalytic enantioselective direct Mannich-type reaction, aza-FriedelCrafts reaction, and direct aminalization. As an approach for chiral ligands, a Strecker-type reaction was also developed with the use of chiral BINSA-lanthanum(III) complexes. Moreover, we developed a practical synthesis of optically pure 3,3-Ar2-BINSAs.

Novelty and originality of this research

Chiral BINSA is simple and highly useful compound with extremely strong Brnsted acidity, and provide a variety of functions as chiral catalysts.

Application and research area for Industry collaboration

Development of super acids and efficient synthesis of amino acid derivatives.

Key Takeaway

Chiral BINSA-catalyzed asymmetric catalysis

Keywords

sulfonic acid, BINSA, catalyst, ligand, ammonium salt, cluster, asymmetric catalysis

Technologies

  • Synthetic method of highly active BINSA catalysts
  • Synthesis of natural and unnatural amino acids

Patents

  • JP5408662

Monographs, Papers and Articles

  • Manabu Hatano, Toshikatsu Maki, Katsuhiko Moriyama, Manabu Arinobe, Kazuaki Ishihara:J. Am. Chem. Soc. 2008, 130(50), 16858–16860.
  • Manabu Hatano, Takuya Ozaki, Keisuke Nishikawa, Kazuaki Ishihara:J. Org. Chem. 2013, 78(20), 10405-10413.
  • Manabu Hatano, Kazuaki Ishihara:Asian J. Org. Chem. 2014, 3(4), 352-365.
  • 波多野 学、西川 圭祐、石原 一彰:TCIメール 2014, No. 160, 2-23.