Organocatalytic Cycloaddition Reactions and Mechanistic Investigations

• Applicants: Privatdozent Dr.-Ing. Armin Ofial; Professor Dr. Hendrik Zipse
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2019 to 2022
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 410831260

• Final Report Year: 2022

Final Report Abstract

The Lu reaction is used for the synthesis of organic compounds containing five-membered ring systems. Phosphines are used as catalysts in this reaction, and electron-deficient alkenes, allenes and alkynes are used as building blocks. Kinetic measurements and theoretical calculations have now been combined to quantify the reactivities of these catalysts and building blocks. This makes it easier to predict the potential applications of the Lu reaction for the preparation of new cyclic compounds.

Publications

• “Nucleophilie von Glutathion als Bindeglied zur Reaktivität von Michael-Akzeptoren“. Angew. Chem. 2019, 131, 17868 - 17872; Angew. Chem. Int. Ed. 2019, 58, 17704 - 17708
  R. J. Mayer, A. R. Ofial
  (See online at https://doi.org/10.1002/ange.201909803 https://doi.org/10.1002/anie.201909803)
• "Construction of α,α-disubstituted α-Amino Acid Derivatives via aza-Morita-Baylis-Hillman Reactions of 2-Aminoacrylates with Activated Olefins". ChemCatChem 2020, 12, 1143 - 1147
  H.-Z. Gui, H. Jangra, B. Mao, T.-Y. Wang, H. Yi, Q. Xu, Y. Wei, H. Zipse, M. Shi
  (See online at https://doi.org/10.1002/cctc.201901987)
• "Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with allenoates and mechanistic studies". Catal. Sci. Technol. 2020, 9, 3959 - 3964
  X.-Y. Wu, H.-Z. Gui, H. Jangra, Y. Wei, H. Zipse, M. Shi
  (See online at https://doi.org/10.1039/D0CY00092B)
• "Reactivities of allenic and olefinic Michael acceptors towards phosphines". Chem. Commun. 2022, 58, 3358 - 3361
  F. An, H. Jangra, Y. Wei, M. Shi, H. Zipse, A. R. Ofial
  (See online at https://doi.org/10.1039/D1CC06786A)