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000742161 019__ $$a931592181$$a932333233
000742161 020__ $$a9783319230061$$qelectronic book
000742161 020__ $$a3319230069$$qelectronic book
000742161 020__ $$z9783319230054
000742161 0247_ $$a10.1007/978-3-319-23006-1$$2doi
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000742161 035__ $$aSP(OCoLC)922528465$$z(OCoLC)931592181$$z(OCoLC)932333233
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000742161 049__ $$aISEA
000742161 050_4 $$aQP550
000742161 08204 $$a547$$223
000742161 1001_ $$aNanteuil, Florian de,$$eauthor.
000742161 24510 $$aSynthesis and reactivity of donor-acceptor substituted aminocyclopropanes and aminocyclobutanes$$h[electronic resource] /$$cFlorian de Nanteuil.
000742161 264_1 $$aCham :$$bSpringer,$$c[2016]
000742161 300__ $$a1 online resource.
000742161 336__ $$atext$$btxt$$2rdacontent
000742161 337__ $$acomputer$$bc$$2rdamedia
000742161 338__ $$aonline resource$$bcr$$2rdacarrier
000742161 4901_ $$aSpringer theses
000742161 500__ $$aDoctoral thesis accepted by EPFL, the Swiss Federal Institute of Technology in Lausanne, Switzerland.
000742161 504__ $$aIncludes bibliographical references.
000742161 5050_ $$aParts of this thesis have been published in: ; Supervisor's Foreword; Abstract; Contents; Abbreviations, Acronyms and Symbols; 1 Introduction; 1.1 Introduction; 1.2 Importance of Nitrogen-Substituted Four, Five and Six-Membered Rings; 1.2.1 Four-Membered Rings; 1.2.2 Five-Membered Rings; 1.2.3 Six-Membered Rings; 1.3 Cyclopropanes and Cyclobutanes: General Structure and Reactivity; 1.3.1 Cyclopropanes; 1.3.2 Cyclobutanes; 1.4 Donor-Acceptor Substituted Cycloalkanes; 1.4.1 Structure and Reactivity; 1.4.2 Formal Cycloaddition versus Annulation
000742161 5058_ $$a1.4.3 Synthesis and Reactivity of Donor-Acceptor Substituted Cyclopropanes1.4.3.1 Synthesis of Donor-Acceptor Substituted Cyclopropanes; 1.4.3.2 Friedel-Crafts Alkylation; 1.4.3.3 Lewis Acid Mediated [3 + 2] Annulation of Olefins and Alkynes; 1.4.3.4 Lewis Acid Mediated [3 + 2] Annulation of Carbonyl Compounds; 1.4.3.5 Lewis Acid Mediated [3 + 2] Annulations with Other Dipolarophiles; 1.4.3.6 [3 + 2] Annulations with Other Modes of Activation; 1.4.3.7 Enantioselective Processes Involving DA Cyclopropanes; 1.4.4 Conclusion; 1.4.5 Donor-Acceptor Substituted Cyclobutanes; 1.4.5.1 Synthesis
000742161 5058_ $$a1.4.5.2 [4 + 2] Annulations1.4.6 Conclusion; 1.5 Reactivity of Nitrogen-Substituted Small Cycloalkanes; 1.5.1 Cyclopropanes; 1.5.2 Cyclobutanes; 1.5.3 Conclusion; 1.6 Work in the Group; 1.7 Goal of the Project; References; 2 Ring-Opening Reactions of Aminocyclopropanes; 2.1 [3 + 2] Annulation with Enol Ethers [1]; 2.1.1 Discovery of the Reaction and Optimization; 2.1.2 Scope and Limitations; 2.1.3 Mechanism; 2.1.4 Product Modifications; 2.2 [3 + 2] Annulation with Aldehydes; 2.3 [3 + 2] Annulation with Ketones; 2.4 Friedel-Craft Alkylation of Indoles [15]; 2.4.1 Preliminary Results
000742161 5058_ $$a2.4.2 Synthesis of New Cyclopropane Analogues2.4.3 Optimization of the Reaction; 2.4.4 Scope of the Reaction; 2.4.5 Product Transformations; 2.5 Dynamic Kinetic Asymmetric [3 + 2] Annulation of DA Aminocyclopropanes; 2.5.1 DyKAT: 1st Generation; 2.5.2 DyKAT: 2nd Generation; 2.5.3 DyKAT: 3rd Generation; 2.5.4 Scope of the Reaction; 2.5.5 Origin of Asymmetric Induction; 2.6 Conclusion; References; 3 Synthesis and [4 + 2] Annulation of Aminocyclobutanes; 3.1 Discovery of the [2 + 2] Cycloaddition; 3.1.1 Synthesis of Methylidene Malonates
000742161 5058_ $$a3.1.2 Discovery and Optimization of the [2 + 2] Cycloaddition3.2 Scope and Limitations; 3.2.1 Synthesis of Alkylidene Malonates; 3.2.2 Synthesis of Enimides; 3.2.3 Scope of the Reaction; 3.2.4 Product Modification; 3.3 [4 + 2] Annulation of Aminocyclobutanes; 3.3.1 Optimization of the Reaction; 3.3.2 Synthesis of Substrates; 3.3.3 Scope and Limitations; 3.4 Conclusion; References; 4 Conclusions and Outlook; References; 5 Experimental Part; 5.1 General Methods; 5.2 [3 + 2] Annulation with Enols Ethers; 5.3 [3 + 2] Annulation with Aldehydes; 5.4 [3 + 2] Annulation with Ketones
000742161 506__ $$aAccess limited to authorized users.
000742161 520__ $$aThis 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.
000742161 588__ $$aVendor-supplied metadata.
000742161 650_0 $$aBioorganic chemistry.
000742161 650_0 $$aPharmaceutical chemistry.
000742161 650_0 $$aAmino acids$$xSynthesis.
000742161 650_0 $$aAmino acids$$xReactivity.
000742161 650_0 $$aCyclopropane.
000742161 650_0 $$aCyclobutane.
000742161 77608 $$iPrint version:$$ade Nanteuil, Florian$$tSynthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes$$dCham : Springer International Publishing,c2015$$z9783319230054
000742161 830_0 $$aSpringer theses.
000742161 85280 $$bebk$$hSpringerLink
000742161 85640 $$3SpringerLink$$uhttps://univsouthin.idm.oclc.org/login?url=http://link.springer.com/10.1007/978-3-319-23006-1$$zOnline Access$$91397441.1
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000742161 980__ $$aEBOOK
000742161 980__ $$aBIB
000742161 982__ $$aEbook
000742161 983__ $$aOnline
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