Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes (inbunden)
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Format
Inbunden (Hardback)
Språk
Engelska
Antal sidor
315
Utgivningsdatum
2015-10-05
Upplaga
1st ed. 2015
Förlag
Springer International Publishing AG
Illustratör/Fotograf
Bibliographie 150 schwarz-weiße und 4 farbige Abbildungen
Illustrationer
XVII, 315 p.
Dimensioner
234 x 156 x 19 mm
Vikt
645 g
Antal komponenter
1
Komponenter
1 Hardback
ISBN
9783319230054

Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes

av Florian De Nanteuil
Inbunden,  Engelska, 2015-10-05
1505
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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.
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Innehållsförteckning

Introduction.- Ring-Opening Reactions of Aminocyclopropanes.- Synthesis and [4+2] Annulation of Aminocyclobutanes.- Conclusions and Outlook.- Experimental Part.

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