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Séminaire Chimie ED459

Design of single and supramolecularly assembled organocatalysts for green sustainable chemistry

Prof. Keiji Maruoka (Kyoto University, Japan)

published on , updated on

Le Mardi 22 Mai 2012 à 11h
UM2, salle de cours SC-11.01

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, and some of them are found to be quite useful for the development of environmentally-benign asymmetric organic transformations under essentially neutral conditions. Very recently, we have found that certain cis-diamine-based bifunctional organocatalysts in the presence or absence of carboxylic acid additives allow the complete product selectivity, giving both enantiomeric products from the single chiral catalyst. The supramolecular assembly of such catalysts and additives is conceivable to explain the product selectivity. The detail of such new catalyst design in addition to the practical application to environmentally-benign 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. Chimia 2007, 61, 263.
(e) Maruoka, K.; Ooi, T.; Kano, T. Chem. Commun. 2007, 1487.
(f) Maruoka, K. Org. Proc. Res. Devel. 2008, 12, 679.
(g) Maruoka, K. Chem. Record. 2010, 10, 254.

2. PTC: (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.
(g) Hashimoto, T.; Fukumoto, K.; Abe, N.; Sakata, K.; Maruoka, K. Chem. Comm. 2010, 46, 7593.

3. Bifunctional Catalysts: (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.
(e) Kano, T.; Mii, H.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 3450.
(f) Kano, T.; Tanaka, Y.; Osawa, K.; Yurino, T.; Maruoka, K. Chem. Comm. 2009, 19956.
(g) Kano, T.; Kumano, T.; Sakamoto, R.; Maruoka, K. Chem. Sci. 2010, 1, 499.
(h) Moteki, S. A.; Xu, S.; Arimitsu, S.; Maruoka, K. J. Am. Chem. Soc. ASAP.

4. Brønsted Acids: (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.

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