研究领域

Organische Chemie

The research in our group spans the field of organic chemistry from mechanistic studies to synthetic methodology and the synthesis of natural products as well as of structurally intriguing heterocyclic compounds. The central focus of the research is the design of new methods for the synthesis of bioactive and synthetically versatile compounds. We have a series of collaborations to evaluate our target molecules with teams of biochemists or physicists. As a result, our work involves a wide range of expertise in organic synthesis, heterocyclic chemistry, asymmetric synthesis and organometallic chemistry: lithiated alkoxyallenes are extremely versatile building blocks that have both nucleophilic and electrophilic centres. By taking advantage of this property highly functionalized heterocycles can be synthesized. We currently focus on the synthesis of enantiopure furan, pyrrole, 1,2-oxazine and spiroketal derivatives. Target compounds are glycosidase inhibitors, carbohydrate mimetics, aminosugar derivatives and rare monosaccharides. It was found that gold nanoparticles decorated with sulfated carbohydrate mimetics are extremely good multivalent selectin ligands with IC50 values in the subnanomolar range. new multicomponent reactions with lithiated alkoxyallenes as crucial precursor lead to novel highly substituted pyridine, pyrimidine and oxazole derivatives. The substitution pattern of these substrates allows us to selectively couple each molecule via metal-catalyzed coupling reactions in order to synthesize a variety of nano-sized oligoaryl-hetaryl conjugates as well as novel bipyridine and terpyridine derivatives. Multivalent heterocyclic moieties are also constructed to study their properties on graphite and metal surfaces by STM and SMF. samarium diiodide is an electron-transfer reagent for chemo- and stereoselective carbon-carbon bond formation. We take advantage of this reactivity to synthesize steroid analogues, some of which have shown desired biological activity. We have also demonstrated that this reagent can be successfully used for the synthesis of highly substituted indole and pyrrole derivatives as well as a variety of medium-sized (7-, 8- and 9-membered) rings. These efforts culminated in a short and extremely efficient total synthesis of the magic natural product strychnine. Another aspect of our research focuses on the synthesis of peptide analogues using methodology developed earlier in our group. Starting from donor-acceptor-substituted cyclopropanes in the presence of sulfur and CH-acidic components we are able to generate thiophene-derived amino acids (Gewald reaction), which share isosteric properties with natural dipeptides. These building blocks can be used in the synthesis of novel macrocycles as well as peptidomimetics. alkenyl and (het)aryl nonaflates are very useful intermediates for cross-coupling reactions. Although slightly more reactive compared to the related triflates they are more stable and available through selective and inexpensive methods. Palladium catalyzed reactions provide very useful coupling products, in particular novel pyridine derivatives as well as polycyclic compounds.

近期论文

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D. Trawny, V. Kunz, H.-U. Reißig* Modular Syntheses of Star-Shaped Pyridine, Bipyridine, and Terpyridine Derivatives by Employing Sonogashira Reactions Eur. J. Org. Chem. 2014, 6295 – 6302. D. Reich, D. S. Müller, L. Schefzig, R. Zimmer,* H.-U. Reißig* One-Pot Generation of C≡X Bonds from Methyl 2-Siloxycyclopropanecarboxylates: Simple Syntheses of Functionalized Nitriles and Alkynes Synlett 2014, 25, 2265 – 2270. H.-U. Reißig*, R. Zimmer Münchnone – 50 Jahre und ein bisschen weiser Angew. Chem. 2014, 126, 9864 – 9866. H.-U. Reißig*, R. Zimmer Münchnones – New Facets after 50 Years Angew. Chem. Int. Ed. 2014, 53, 9708 – 9710. M. Jasiński, G. Mlostoń, M. Stolarski, W. Costa, M. Domínguez, H.-U. Reißig* Reactions of Cycloaliphatic Thioketones and Their Oxo Analogues with Lithiated Methoxyallene: A New Approach to Vinylthiiranes Chem. Asian J. 2014, 9, 2641 – 2648. D. Trawny, L. Vandromme, J. P. Rabe,* H.-U. Reissig* The Side Chain Makes the Difference: Investigation of the 2D Self-Assembly of 1,3,5-Tris[4-(4-pyridinyl)phenyl]benzene Derivatives by Scanning Tunneling Microscopy Eur. J. Org. Chem. 2014, 4985 – 4992. M. Kandziora, H.-U. Reißig* Synthesis of Rigid p-Terphenyl-Linked Carbohydrate Mimetics Beilstein J. Org. Chem. 2014, 10, 1749 – 1758. P. Hommes, C. Fischer, C. Lindner, H. Zipse*, H.-U. Reißig* Extrem starke Lewis-Basen – Synthese und Methylkationaffinitäten von Dimethylamino-substituierten Terpyridinen Angew. Chem. 2014, 126, 7778 – 7782. P. Hommes, C. Fischer, C. Lindner, H. Zipse*, H.-U. Reißig* Unprecedented Strong Lewis Bases – Synthesis and Mehtyl Cation Affinities of Dimethylamino-Substituted Terpyridines Angew. Chem. Int. Ed. 2014, 53, 7647 – 7651. D. Gladow, S. Doniz-Kettenmann, H.-U. Reißig* 1,3-Dipolar Cycloadditions of Ethyl 2-Diazo-3,3,3-trifluoropropanoate to Alkynes and [1,5] Sigmatropic Rearrangements of the Resulting 3H-Pyrazoles: Synthesis of Mono-, Bis- and Tris(trifluoromethyl)-Substituted Pyrazoles Helv. Chim. Acta, 2014, 97, 808 – 821. D. Gladow, H.-U. Reißig* Perfluoroalkyl-Substituted Thiophenes and Pyrroles from Donor-Acceptor Cyclopropanes and Heterocumulenes: Synthesis and Exploration of their Reactivity J. Org. Chem. 2014, 79, 4492 – 4502. L. Bouché, H.-U. Reißig* Synthesis of Di- and Trivalent Carbohydrate Mimetics with Oxepane Substructure by Employing Copper-Catalyzed [3+2] Cycloadditions of Alkynes with Azidooxepanes Eur. J. Org. Chem. 2014, 3697 – 3703. M. Wilsdorf, H.-U. Reißig* Eine konvergente Totalsynthese des Telomerase-Inhibitors (±)-γ-Rubromycin Angew. Chem. 2014, 126, 4420 – 4424. M. Wilsdorf, H.-U. Reißig* A Convergent Total Synthesis of the Telomerase Inhibitor (±)-γ-Rubromycin Angew. Chem. Int. Ed. 2014, 53, 4332 – 4336. M. Domínguez, H.-U. Reißig* New 4-Pyridyl Nonaflates as Precursors for Push-Pull Solvatochromik Dyes Synthesis 2014, 46, 1110 – 1106. R. Zimmer, H.-U. Reißig* Alkoxyallenes as Building Blocks for Organic Synthesis Chem. Soc. Rev. 2014, 43, 2888 – 2903. M. K. Bera, M. Domínguez, P. Hommes, H.-U. Reißig* The Flögel-Three-Component Reaction with Dicarboxylic Acids - An Approach to Bis(β-alkoxy-β - ketoenamides) for the Synthesis of Complex Pyridine and Pyrimidine Derivatives Beilstein J. Org. Chem. 2014, 10, 394 – 404. L. Bouché, M. Kandziora, H.-U. Reißig* Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics Beilstein J. Org. Chem. 2014, 10, 213 – 223. M. Jasiński, E. Moreno-Clavijo, H.-U. Reißig* Synthesis of a Series of Enantiopure Polyhydroxylated Bicyclic N-Heterocycles from an l-Erythrose Derived Nitrone and Alkoxyallenes Eur. J. Org. Chem. 2014, 442 – 454.