0940 - 1020 Keiji Maruoka

Design of High-Performance Organocatalysts for Catalytic Asymmetric Synthesis

The design of new catalysts and new organic transformations in an environmentally benign manner is increasingly important in recent years for the construction of new and useful chiral molecules from simple organic resources. In this context, organocatalysis has recently emerged as a field of research providing practical alternative or complementary technologies to the more traditional transition metal catalyzed systems. Accordingly, we have rationally designed various environmentally benign chiral organocatalysts such as chiral phase transfer catalysts, chiral bifunctional organocatalysts, and chiral Brønsted acid catalysts, starting from commercially available optically pure binaphthol.^[1] These binaphthyl-modifiedchiral organocatalysts have been successfully applied for the development of various types of new catalytic asymmetric transformations. ^[2-4] Quite recently, a new, chiral bifunctional phase transfer catalyst based on a binaphthyl backbone has been designed and successfully applied to hitherto unknown, base-free asymmetric reactions under essentially neutral conditions. ^[2f] A new approach for the design of chiral bifunctional organocatalysts derived from a cis-diamine core structure has been also developed in a highly practical manner. ^[3d] The detail of such new catalyst design in addition to the application to catalytic asymmetric transformations will be presented in my lecture. 

References

[1]  Reviews: (a) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656.(b) Ooi, T.; Maruoka,

K. Angew. Chem. Int. Ed. 2007,  46, 4222. (c) Ooi, T.; Maruoka, K. Aldrichimica Acta 2007, 40, 77. (d)

Maruoka, K.; Ooi, T.; Kano, T. Chem. Commun. 2007, 1487. (e) Maruoka, K. Org. Proc. Res.

Devel. 2008, 12, 679.

[2]   (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. (b) Kitamura, M.;

Shirakawa, S.; Maruoka, K. Angew. Chem. Int. Ed. 2005, 44, 1549. (c) Ooi, T.; Uematsu, Y.; Maruoka, 

K. J. Am. Chem. Soc. 2006, 128, 2548. (d) Wang, X.; Kitamura, M.; Maruoka, K. J. Am. Chem.

Soc., 2007, 129, 1038. (e) He, R.; Wang, X.; Hashimoto, T.; Maruoka, K. Angew. Chem. Int.

Ed., 2008, 47, 9466. (f) He, R.; Shirakawa, S.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 16620.

[3]   (a) Kano, T.; Yamaguchi, Y.; Tokuda, O.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 16408. (b)

Kano, T.; Ueda, M.; Takai, J.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 6046. (c) Kano, T.; Ueda,

M.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 3728. (d) Nakayama, K.; Maruoka, K. J. Am. Chem.

Soc. 2008, 130, 17666.

[4]   (a) Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2007, 129, 10054. (b) Hashimoto, T.; Naganawa,

Y.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 2434. (c) Hashimoto, T.; Hirose, M.; Maruoka, K. J. Am.

Chem. Soc. 2008, 130, 7756. (d) Hashimoto, T.; Uchiyama, N.; Maruoka, K. J. Am. Chem

Soc. 2008, 130, 14380.