@article{742161,
      recid = {742161},
      author = {Nanteuil, Florian de,},
      title = {Synthesis and reactivity of donor-acceptor substituted  aminocyclopropanes and aminocyclobutanes [electronic  resource] /},
      pages = {1 online resource.},
      note = {Doctoral thesis accepted by EPFL, the Swiss Federal  Institute of Technology in Lausanne, Switzerland.},
      abstract = {This thesis presents a general approach to accessing  nitrogen-substituted hetero- and carbocycles. In short, the  annulation reactions developed in the thesis make it  possible to access nitrogen-substituted four-, five- and  six-membered rings, all essential building blocks for the  synthesis of bioactive molecules. Many natural products  display a saturated polycyclic core allowing a well-defined  arrangement of functional groups in space. As such, they  can interact with biological targets with a high degree of  affinity and selectivity, surpassing many synthetic drugs.  Nevertheless, the efficient synthesis of such complex ring  systems poses a challenge for organic chemistry. Through  careful tuning of the electronic properties of a nitrogen  donor group and a diester acceptor group, the first [3+2]  annulation reaction between aminocyclopropanes and enol  ethers or carbonyl compounds is now possible. The reaction  proceeded under mild catalytic conditions, and the building  blocks obtained can be found at the core of bioactive  alkaloids, drugs such as Ramipril and biomolecules such as  DNA and RNA. Thanks to the dynamic kinetic asymmetric  annulation of aminocyclopropanes with enol ethers and  aldehydes, access to enantioenriched compounds is also now  possible. Lastly, a synthesis of donor-acceptor  aminocyclobutanes via [2+2] cycloaddition using a cheap  iron catalyst was developed, allowing them to be used in  [4+2] annulations to access cyclohexylamines.},
      url = {http://library.usi.edu/record/742161},
      doi = {https://doi.org/10.1007/978-3-319-23006-1},
}