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法國波爾多大學(xué) ISM CSC 化學(xué)
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PhD supervisor : Prof. Patrick Y. Toullec. Email:  patrick.toullec@u-bordeaux.frThe PhD research will spread over a maximum of 4 years and will be conducted at the University of Bordeaux at the Institute of Molecular Sciences (ISM, CNRS Unit 5255) under the direction of Prof. Patrick Toullec, an expert in the field of organic synthesis, organometallic and organic catalysis. Summary of research project : Selective cycloisomerization and cycloaddition transformations represents a class of reactions enabling the synthesis of functionalized carbo- and heterocycles of higher complexity starting from simple organic precursors in a single step with maximal atom economy. Metal-catalyzed cycloisomerization involving highly active carbophilic Lewis acids[1] (Au, Pt, Ir, Rh etc) have played a central role in the development of enantioselective variants[2] of these transformations. Much less is known concerning organocatalyzed cycloisomerization reactions[3] and very few examples deal with Brønsted acid- catalyzed asymmetric cycloisomerizations resulting from the initial activation of a carbon-carbon triple bond by a proton.[4] Our group has a long-standing experience in the field of carbophilic Lewis acids and their application in homogeneous catalysis[5] as well as in electrophile-induced carbocyclization reactions.[6] Recently, we started a research program[7] devoted to the asymmetric Brønsted acid cycloisomerization featuring the activation of alkyne and phenol functions. The project will deal with the development of new, enantioselective cycloisomerization and cycloaddition reactions enabling the synthesis of highly complex, polycyclic molecules via a metal-free approach. The key step of the project involves the electrophilic activation of quinones and (vinylidene) quinone methides in the presence of chiral Bronsted acid catalysis.The application of these strategies to the total synthesis of natural products will be also targeted in a second phase of the project. During this four-year PhD, group meetings will take place weekly in presence or by zoom, along with regular individual interviews in collaboration with Prof. Patrick Toullec. Publications of the results in high- impact-factor scientific journals and communications in local and international meetings. Preparation to job applications in China during the 4th year will be scheduled. Desired profile : A motivated Master student in organic chemistry willing to specialize in asymmetric organocatalysis. A good command of characterization techniques (including Nuclear Magnetic Resonance Spectroscopy, Mass Spectrometry and Single-Crystal X-ray Crystallography along with Chiral High Performance Liquid Chromatography and Circular Dichroism) is mandatory. A good command of French or English is expected from the candidate (TOEFL PbT: minimum 550, or TOEFL ibT: minimum 79, or IELTS: minimum 6.5, or TOEIC: minimum 685, or show proof of CEFR level B2 in English or French). [1] a) A. Fürstner, P. W. Davies Angew. Chem. Int. Ed. 2007, 46, 3410. b) D. J. Gorin, F. D. Toste Nature 2007, 446, 395. c) P. Y. Toullec, V. Michelet Top. Curr. Chem. 2011, 302, 31. [2] Toullec, P. Y.; Pradal, A.; Michelet, V. «Recent Developments in Asymmetric Catalysis» in “Gold Catalysis: An Homogeneous Approach”, Catalytic Science Series, vol. 13, Eds. Toste, F. D.; Michelet, V., 2014, Imperial College Press, Chap. 12, 445. [3] For seminal examples, see: a) S. Rendeler, D. W. C. MacMillan J. Am. Chem. Soc. 2010, 132, 5027. b) R. R. Knowles, S. Lin, E. N. Jacobsen J. Am. Chem. Soc. 2010, 132, 5030. [4] a) K. Ishihara, S. Nakamura, H. Yamamoto J. Am. Chem. Soc. 1999, 121, 4906. b) N. D. Shapiro, V. Rauniyar, G. L. Hamilton, J. Wu, F. D. Toste Nature 2011, 470, 245. [5] a) A. Pradal, S. Gladiali, V. Michelet, P. Y. Toullec Chem. Eur. J. 2014, 20, 7128. b) C. M. Chao, M. Vitale, P. Y. Toullec, J.-P. Genêt, V. Michelet, Chem. Eur. J. 2009, 15, 1319. c) C.-M. Chao, D. Beltrami, P. Y. Toullec, V. Michelet Chem. Comm. 2009, 6988. [6] C. Grandclaudon, V. Michelet, P. Y. Toullec Org. Lett. 2016, 18, 676. [7] a) Gicquiaud, J.; Hacihasanoglu, A.; Hermange, P.; Sotiropoulos, J. M.; Toullec, P. Y. Adv. Synth. Catal. 2019, 361, 2025. b) Gicquiaud, J.; Abadie, B.; Dhara, K.; Berlande, M.; Hermange, P.; Sotiropoulos, J. M.; Toullec, P. Y. Chem. Eur. J. 2020, 26, 16266. |
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