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BL
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| Record Number
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864754
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| Main Entry
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Iorio, Nicola Di
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| Title & Author
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New organocatalytic strategies for the selective synthesis of centrally and axially chiral molecules /\ Nicola Di Iorio.
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| Publication Statement
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Cham, Switzerland :: Springer,, 2018.
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| Series Statement
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Springer theses
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| Page. NO
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1 online resource
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| ISBN
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3319749145
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: 9783319749143
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9783319749136
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| Notes
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"Doctoral thesis accepted by the University of Bologna, Italy."
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| Bibliographies/Indexes
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Includes bibliographical references.
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| Contents
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Intro; Supervisor's Foreword; Preface; Parts of this thesis have been published in the following articles:; Acknowledgements; Contents; Abbreviations; 1 Introduction; 1.1 Chirality and its Forms: Central, Axial and UnconventionalID=""Fn1""For further reading on chirality see: Eliel and Wilen [1].; 1.1.1 Central Chirality; 1.1.2 Axial Chirality; 1.1.3 Helical Chirality; 1.1.4 Planar Chirality; 1.2 Pursuing Enantiopure Chiral Molecules: Asymmetric Organocatalysis; 1.2.1 Aminocatalysis: Enamine and Iminium Ion; 1.2.2 Nucleophilic Catalysis.
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1.2.3 Brønsted Acid and Base CatalysisID=""Fn12""(a) For an exhaustive reading on Brønsted acid/base catalysis see: Rueping et al. [51] (b) Science of synthesis "Asymmetric organocatalysis 2 -- Brønsted base and acid catalysis, and additional topics", Thieme, 2012.; 1.2.4 Asymmetric Counterion-Directed and Phase-Transfer Catalysis; 1.2.5 Hydrogen-Bonding CatalysisID=""Fn16""For reviews see: (a) Doyle and Jacobsen [65]; (b) Knowles and Jacobsen [66].; 1.2.6 Dual Catalysis: Bifunctional and Cooperative; References.
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2 The Vinylogous Reactivity of Oxindoles Bearing Non-symmetric 3-Alkylidene Groups2.1 Vinylogy; 2.2 Results and Discussion; 2.3 Conclusions; 2.4 Experimental Section; 2.4.1 General Information; 2.4.2 Preparation of Deuterated Substrates; 2.4.3 General Procedure for the Preparation of Alkylidenoxindoles; 2.4.4 General Procedure for the Vinylogous Michael Addition of Non-symmetric 3-Alkylidene Oxindoles to Nitroalkenes; References; 3 Targeting the Remote Control of Axial Chirality in N-(2-tert-butylphenyl)Succinimides via a Desymmetrization Strategy.
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3.1 Desymmetrization as a Tool for Asymmetric Synthesis3.2 Results and Discussion; 3.3 Conclusions; 3.4 Experimental Section; 3.4.1 General Information; 3.4.2 Determination of the Barrier to Racemization of the Chiral Axis for Compound 137a; 3.4.3 General Procedure for the Vinylogous Michael Addition of Cyclic Enones to N-Arylmaleimmides; 3.4.4 General Procedure for the Desymmetrization of Maleimides with Different Nucleophiles; 3.4.5 General Procedure for the Desymmetrization of Maleimides with 3-Aryl Oxindoles; References.
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4 Direct Catalytic Synthesis of C(Sp2)-C(Sp3) Atropisomers with Simultaneous Control of Central and Axial Chirality4.1 Forging a Stereogenic Axis; 4.2 Results and Discussion; 4.3 Conclusions; 4.4 Experimental Section; 4.4.1 General Information; 4.4.2 General Procedure for the Synthesis of 4-Substituted Indenones; 4.4.3 Synthesis of Naphthol Derivatives; 4.4.4 General Procedure for the Synthesys of 8-Arylnaphthalen-2-Ol; 4.4.5 Determination of the Barrier to Racemization Relative to the Naphthol-Phenantrene Stereogenic Axis for Compound 244.
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| Abstract
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This thesis discusses the use of asymmetric organic catalysis for the direct enantioselective synthesis of complex chiral molecules, and by addressing the many aspects of both vinylogy and atropisomerism, it appeals to researchers and scholars interested in both areas. Organocatalysis is a relatively modern and "hot" topic in the chemical community; it is constantly expanding and its use has been extended to interesting areas like vinylogous reactivity and atropisomerism. Vinylogous systems are very important for their synthetic applications but also pose a number of challenges, the most notable of which are their reduced reactivity and the reduced stereocontrol at these positions. On the other hand, atropisomeric systems are even more important because of the huge potential they have as drugs, ligands and catalysts. Chemists have only recently "recognized" the importance of these two areas and are focusing their efforts on studying them and the challenges they pose. This thesis offers an extensive introduction on the general aspects of chirality and organocatalysis and an equally extensive experimental section that allow nonexperts to understand the discussion section and reproduce the experiments.
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| Subject
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Asymmetric synthesis.
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Enantioselective catalysis.
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Asymmetric synthesis.
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Biochemistry.
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Catalysis.
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Enantioselective catalysis.
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Organic chemistry.
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| Subject
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SCIENCE-- Chemistry-- Organic.
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| Dewey Classification
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547/.215
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| LC Classification
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QD505
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