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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.
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.
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