Mechanistic Studies of Donor-acceptor Cyclopropanes PDF Download
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Author: Tristan Chidley
Publisher:
ISBN:
Category :
Languages : en
Pages : 252
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Book Description
Cyclopropane 1,1-diesters have been investigated as a source of donor-acceptor cyclopropanes, providing an understanding of the mechanism of reaction between these cyclopropanes and nitrosoarenes, as well as azo dicarboxylates. Cross-over experiments have been utilized to provide key pieces of experimental evidence that help generate a theoretical model of the reactions. By understanding these reactions with precision, the avenue to expand the reaction scope and develop other useful reactions is opened up. This allows the chemistry to be better utilized, providing easier access to important molecules when needed, and contributes to advancing the field of synthetic organic chemistry. In addition, cyclobutane 1,1-diesters were also investigated as a source of donor-acceptor cyclobutanes. Specifically, their use in cycloaddition reactions has been developed to include the reaction of cyclobutanes with cis-diazenes, providing access to hexahydropyridazines. These compounds are synthesized in an efficient manner and are known to contain biologically active properties.
Author: Tristan Chidley
Publisher:
ISBN:
Category :
Languages : en
Pages : 252
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Book Description
Cyclopropane 1,1-diesters have been investigated as a source of donor-acceptor cyclopropanes, providing an understanding of the mechanism of reaction between these cyclopropanes and nitrosoarenes, as well as azo dicarboxylates. Cross-over experiments have been utilized to provide key pieces of experimental evidence that help generate a theoretical model of the reactions. By understanding these reactions with precision, the avenue to expand the reaction scope and develop other useful reactions is opened up. This allows the chemistry to be better utilized, providing easier access to important molecules when needed, and contributes to advancing the field of synthetic organic chemistry. In addition, cyclobutane 1,1-diesters were also investigated as a source of donor-acceptor cyclobutanes. Specifically, their use in cycloaddition reactions has been developed to include the reaction of cyclobutanes with cis-diazenes, providing access to hexahydropyridazines. These compounds are synthesized in an efficient manner and are known to contain biologically active properties.
Author: Prabal Banerjee
Publisher: John Wiley & Sons
ISBN: 3527349871
Category : Science
Languages : en
Pages : 469
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Book Description
Facilitate milder, simpler reactions in organic synthesis with this cutting-edge family of building blocks Donor-Accepted Cyclopropanes, or DACs, have attracted a resurgence of interest from organic chemists in recent decades for their role in facilitating various reactions such as cycloadditions, annulations, ring-opening and enantioselective transformations. The structural arrangement of DACs leads to milder, simpler reaction conditions, which have made them indispensable for a range of fundamentally and industrially important processes. Donor-Acceptor Cyclopropanes in Organic Synthesis covers comprehensively the chemistry and applications of this compound class. The result is an invaluable guide for any researcher looking to bring DACs to bear in their own areas of research or development. Readers will also find: A brief introduction of the history and reactivity of DACs Detailed discussion of reactions including Lewis acid-catalyzed cycloadditions, metal-free activation, asymmetric transformations, organocatalysis, and many more Application of DACs in natural product synthesis and pharmaceutical/agrochemical research Donor-Acceptor Cyclopropanes in Organic Synthesis is ideal for organic chemists, experts in catalysis, pharmaceutical researchers, and any other scientists interested in facilitating milder, simpler reactions.
Author: Dennis P. Curran
Publisher: John Wiley & Sons
ISBN: 3527615229
Category : Science
Languages : en
Pages : 294
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Book Description
As little as a decade ago, radicals were regarded as interesting reactive intermediates with little synthetic use. However, recent results show that radicals have an enormous potential for applications in stereoselective reactions - it's all a matter of knowing what method to use and how to apply it. Three world experts in the field have combined their expertise and present the concepts to understand and even to predict the course of stereoselective radical reactions. In addition, guidelines are established which will enable the readers to plan and carry out their own stereoselective syntheses with radicals. A comprehensive list of references provides an easy access to the primary literature. The Stereochemistry of Radical Reactions is a highly topical introduction to this burgeoning field of research. Both advanced students and researchers active in the field will welcome this book as a source of concepts and ideas.
Author: Alexander Kreft
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Book Description
Author: Ming Yu
Publisher:
ISBN:
Category : Cyclopropane
Languages : en
Pages :
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Book Description
Author: Prabal Banerjee
Publisher: John Wiley & Sons
ISBN: 3527835644
Category : Science
Languages : en
Pages : 469
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Book Description
Donor-Acceptor Cyclopropanes in Organic Synthesis Facilitate milder, simpler reactions in organic synthesis with this cutting-edge family of building blocks Donor-Accepted Cyclopropanes, or DACs, have attracted a resurgence of interest from organic chemists in recent decades for their role in facilitating various reactions such as cycloadditions, annulations, ring-opening and enantioselective transformations. The structural arrangement of DACs leads to milder, simpler reaction conditions, which have made them indispensable for a range of fundamentally and industrially important processes. Donor-Acceptor Cyclopropanes in Organic Synthesis covers comprehensively the chemistry and applications of this compound class. The result is an invaluable guide for any researcher looking to bring DACs to bear in their own areas of research or development. Readers will also find: A brief introduction of the history and reactivity of DACs Detailed discussion of reactions including Lewis acid-catalyzed cycloadditions, metal-free activation, asymmetric transformations, organocatalysis, and many more Application of DACs in natural product synthesis and pharmaceutical/agrochemical research Donor-Acceptor Cyclopropanes in Organic Synthesis is ideal for organic chemists, experts in catalysis, pharmaceutical researchers, and any other scientists interested in facilitating milder, simpler reactions.
Author: Huck K. Grover
Publisher:
ISBN:
Category :
Languages : en
Pages : 556
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Book Description
The development and utility of cyclopropanes is an ever-growing field within organic chemistry. In particular, donor-acceptor cyclopropanes have been used in a vast array of methods to access a variety of different hetero and carbocyclic molecular scaffolds. Recently, we have developed a Zn(NTf2)2 catalyzed tandem reaction consisting of a nucleophilic ringopening of 1,1-cyclopropanediesters by 2-alkynyl indoles followed by a Conia-ene ring closure, resulting in the efficient one-step synthesis of tetrahydrocarbazoles. These adducts may be further elaborated to carbazoles. The scope and limitations of this method were determined along with a mechanistic study into the function of the zinc catalyst. In an expansion of our work with 1,1-cyclopropanediesters, we have explored the reactivity and utilization of hemimalonate cyclopropanes. To this end, we have developed two unique methods exploring the self-activating nature of these cyclopropanes under catalyst free conditions. Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce?-azidobutyric acids in good yields. These adducts were hydrogenated to form?-aminobutyric acid (GABA) methyl esters. Additionally, cyclopropane hemimalonates have led to the facile synthesis of?-substituted butanolides. Under microwave irradiation, cyclopropane hemimalonates undergo rapid conversion to butanolides in the presence of inorganic salts with an unprecedented retention of stereochemistry. This unique process, in conjunction with a newly developed crossmetathesis method, has been applied to the total synthesis of the naturally occurring, (R)- dodecan-4-olide. Finally, recent efforts to develop a unified approach to piperidine-containing indole natural products have shown great promise. A preliminary investigation into the prospect of a common synthetic intermediate for the synthesis of a variety of indole alkaloids has led to a synthesis of substituted piperidinones and the corresponding piperidines. These common natural product cores are accessed via a reductive amination/lactamization sequence of dimethyl 3-ethyl-3-formylpimelate. The synthetic utility of this initial study has been displayed in the formal synthesis of (+/- )-quebrachamine.
Author: Cheryl Ann Carson
Publisher:
ISBN:
Category :
Languages : en
Pages : 454
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Book Description
Author: A. C. Knipe
Publisher: John Wiley & Sons
ISBN: 1118941799
Category : Science
Languages : en
Pages : 1023
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Book Description
Organic Reaction Mechanisms 2014, the 50th annual volume in this highly successful and unique series, surveys research on organic reaction mechanisms described in the available literature dated 2014. The following classes of organic reaction mechanisms are comprehensively reviewed: Reaction of Aldehydes and Ketones and their Derivatives Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives Oxidation and Reduction Carbenes and Nitrenes Nucleophilic Aromatic Substitution Electrophilic Aromatic Substitution Carbocations Nucleophilic Aliphatic Substitution Carbanions and Electrophilic Aliphatic Substitution Elimination Reactions Polar Addition Reactions Cycloaddition Reactions Molecular Rearrangements An experienced team of authors compile these reviews every year, so that the reader can rely on a continuing quality of selection and presentation. This volume includes a 5-year cumulative index.
Author: Florian de Nanteuil
Publisher: Springer
ISBN: 9783319370361
Category : Science
Languages : en
Pages : 315
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Book Description
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.
