Organic and Inorganic Seminar: New Reactivity of Strained Rings and Hypervalent Bonds for Synthesis and Chemical Biology

March 19th

חדר סמינרים

9:30

Prof. Jerome Waser, EPF Lausanne

Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.

The development of non-conventional organic synthons stands at the center of our research.1 We harness the power of modern catalysis to unravel the reactivity of energy-loaded molecules, in particular hypervalent iodine reagents2 and strained rings.3 This unique reactivity can then be exploited both for the synthesis of small molecule building blocks and the modification of peptides and proteins. To tackle the issue of selectivity, we also further developed the concept of in situ tethering.4
In this presentation, focus will be on our most recent results in the synthesis and activation of strained ring systems3 and the use of hypervalent iodine reagents for biomolecule functionalization.5
References
(1) https://www.epfl.ch/labs/lcso/research/
(2) (a) D. P. Hari, P. Caramenti, J. Waser, Acc. Chem. Res. 2018, 51, 3212-3225. (b) E. Le Du, J. Waser, Chem. Commun. 2023, 59, 1589-1604.
(3) (a) F. de Nanteuil, F. De Simone, R. Frei, F. Benfatti, E. Serrano, J. Waser, Chem. Commun. 2014, 50, 10912-10928. (b) M.-M. Wang, T. V. T. Nguyen, J. Waser, Chem. Soc. Rev. 2022, 51, 7344-7357.
(4) (a) L. Buzzetti, M. Purins, P. D. G. Greenwood, J. Waser, J. Am. Chem. Soc. 2020, 142, 17334-17339. (b) S. Nicolai, U. Orcel, B. Muriel, P. D. G. Greenwood, L. Buzzetti, M. Puriņš, J. Waser, Synlett 2021, 32, 472-487.
(5) E. M. D. Allouche, E. Grinhagena, J. Waser, Angew. Chem., Int. Ed. 2022, 61, e202112287.

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