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Séminaire Chimie ED459

Synthetic study of biologically interesting natural products based on organocatalytic asymmetric transformations

Prof. Hiyoshizo Kotsuki (Laboratory of Natural Products Chemistry, Faculty of Science, Kochi University, Japan)

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Le Jeudi 20 Septembre 2012 à 13h45
UM2, salle de cours SC-16.01

Recently, a great deal of attention has been focused on the development of new asymmetric catalyses using organic molecules to give chiral organic substances, so-called « asymmetric organocatalysis ». This storm of research interest blossomed just after the turn of this century, and several important contributions have been made. Organocatalytic asymmetric synthesis has several important advantages due to the ready availability, non-toxicity, ease of handling, insensitivity to moisture and oxygen, and environmentally friendly nature of the compounds involved.[1] In our own efforts in this area, we have succeeded in developing several important asymmetric transformations.

In this lecture our recent works related to the following topics will be presented :
1. chiral diamine-catalyzed Robinson-type annulation for the construction of cyclohexenone derivatives bearing a quaternary carbon stereogenic center at the 4-position (Scheme 1),[2]
2. chiral thiourea-catalyzed asymmetric hetero-Diels-Alder reaction of oxindoles under high pressure (Scheme 2),[3]
3. development of aminohydroxyacetone synthons for the use in organocatalytic asymmetric aldol and Mannich reactions (Scheme 3),[4]
4. efficient and mild procedure for the decarboxylative cyanomethyl esterification of arylmalonic acids,[5]
5. new environment-friendly method for Baeyer-Villiger oxidation of cyclobutanones catalyzed by thioureas using H2O2 as an oxidant,[6] and
6. application of these methods to the new short synthesis of biologically interesting natural products.

References

1. Reviews : Kotsuki, H. ; Ikishima, H. ; Okuyama, A. : Heterocycles 2008, 75, 493-529 ; ibid, 757-797.
2. Inokoishi, Y. ; Sasakura, N. ; Nakano, K. ; Ichikawa, Y. ; Kotsuki, H. : Org. Lett. 2010, 12, 1616-1619.
3. Mori, K. ; Yamauchi, T. ; Maddaluno, J. ; Nakano, K. ; Ichikawa, Y. ; Kotsuki, H. : Synlett 2011, 2080-2084.
4. Komatsu, Y. ; Watanabe, R. ; Ikishima, H. ; Nakano, K. ; Ichikawa, Y. ; Kotsuki, H. : Org. Biomol. Chem. 2012, 10, 2993-3001.
5. Sasakura, N. ; Yamauchi, T. ; Nakano, K. ; Ichikawa, Y. ; Kotsuki, H. : Heterocycles 2011, 83, 2773-2778.
6. Sasakura, N. ; Nakano, K. ; Ichikawa, Y. ; Kotsuki, H. : RSC Adv. 2012, 2, 6135-6139.

Scheme 1 (click to enlarge)

Scheme 2 (click to enlarge)

Scheme 3 (click to enlarge)

Contact local IBMM : Dr. Frédéric Lamaty

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