Download or read book Total Synthesis of goniomitine Via a 3 2 Cyclization with Donor acceptor Cyclopropane written by Christian Leonardo Morales and published by . This book was released on 2007 with total page 184 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Cyclopropanes in Organic Synthesis written by Oleg G. Kulinkovich and published by John Wiley & Sons. This book was released on 2015-11-02 with total page 428 pages. Available in PDF, EPUB and Kindle. Book excerpt: This is a practical guidebook about cyclopropanes that thoroughly surveys derivatives and transformations, synthetic methods, and experimental efficiency as a gateway for further research and development in the field. • Provides comprehensive lists and synthetically-oriented synopses of cyclopropane chemistry review references along with publication data on applications in the syntheses of natural and related biologically active compounds • Acts as a resource to help readers better understand cyclopropane applications for the efficient realization of synthetically important organic transformations and popular experimental procedures • Includes new developments and up-to-date information that will lead to original methodologies for complex organic synthesis • Stresses universality, flexibility, and experimental efficiency of a strategy based on preparing cyclopropane derivatives and performing ring cleavage reactions with inexpensive reagents • Focuses on the synthetic potential of cyclopropane applications, for example the synthesis of natural compounds and other target-oriented syntheses via cyclopropane intermediaries, as well on their planning by retrosynthetic analysis
Download or read book Donor Acceptor Cyclopropanes in Organic Synthesis written by Prabal Banerjee and published by John Wiley & Sons. This book was released on 2024-02-09 with total page 469 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.
Download or read book Synthesis and Reactivity of Donor Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes written by Florian de Nanteuil and published by Springer. This book was released on 2016-08-23 with total page 315 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.
Download or read book Exploring the Reactivity of Donor acceptor Cyclopropanes and the Synthesis of Quebrachamine written by Huck K. Grover and published by . This book was released on 2014 with total page 556 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.
Download or read book Total Synthesis of Goniomitine written by Jessica K. Vellucci and published by . This book was released on 2015 with total page 159 pages. Available in PDF, EPUB and Kindle. Book excerpt: Aminal radical intermediates were generated by the method of radical translocation and reacted in C-C bond forming reactions with electronically deficient alkenes (Schiedler et al. Org. Lett. 2012, 14, 6092). Aminal radical intermediates can participate in inter- and intra-molecular reactions using both Bu3SnH and (TMS)3SiH as hydride donors. Carbon-carbon bonds were formed selectively at the aminal carbon in the presence of [alpha]-amino alkyl groups within the molecule. Bicyclic aminals also participated in C-C bond formation affording products in high diastereoselectivity. The application of aminal radical intermediates toward the synthesis of the nitrogen- rich alkaloid goniomitine was investigated. The first generation route involved the development of an acyclic aminal bearing the nitrogen of a 2,3-disubstituted indole and the N-(2-iodobenzyl)formamide nitrogen atom. In the reaction of N-(hydroxymethyl)-N-(2-iodobenzyl)formamide and the indole substrate, none of the desired acyclic aminal was observed. A second generation route utilized an [alpha]-aminoalkyl radical intermediate (generated by radical translocation) to construct the indole framework of goniomitine. The synthesis commenced with a copper-catalyzed Ullmann reaction of an aryl iodide and ethyl-substituted lactam providing the corresponding N-aryl coupling product in 96% yield. Subsequent zinc-catalyzed alkylation with acrylonitrile gave the product in 76% yield, thus installing the quaternary stereocenter of the natural product. Bromination followed by elimination provided the vinyl bromide precursor for the [alpha]-amino radical reaction. Upon treatment with tributyltin hydride and AIBN in refluxing benzene, the substrate underwent homolytic C-Br cleavage, radical translocation and subsequent 5-exo-trig cyclization to provide the desired indoline product as a 3:1 diastereomeric mixture in 83% yield. The indoline was subjected to LiAlH4 to reduce the methyl ester as well as the nitrile to the corresponding primary amine. Upon heating, the amine underwent intramolecular condensation with the lactam, providing the aminal framework of goniomitine. A final oxidation with MnO2 afforded the natural product in a total of six linear steps and 27% overall yield.
Download or read book The Application of Novel Donor Acceptor Cyclopropanes in the Synthesis of Linearly Fused Tricyclic Triazoles written by Michelle Elaine Flisar and published by . This book was released on 2014 with total page 292 pages. Available in PDF, EPUB and Kindle. Book excerpt: Previous work in the Kerr group has shown the su ccess of donor-acceptor cyclopropanes as substrates in a variety of synthetic reactions; this document will apply the use of donor acceptor cyclopropanes in various synthetic reactions. This was done using a 2-substituted 1,1 - cyclopropanediester, in the Overman Rearrangement, which has yet to be explored using DA cyclopropanes. Another useful DA cyclopropane is the novel a cetylene-bearing donor acceptor diester cyclopropanes which would be synthetically useful in a wide variety of reactions. In particular, the Conia-ene cyclization occurred intramolecularly with this alkyne DA cyclopropane with a large library of nucleophiles. Finally, taking this acetylene-bearing DA cyclopropane, it was converted to the hemimalonate version, and subjected to a ring-opening by azide as the nucleophile to generate an alkyl azide; which then underwent a [3+2] dipolar cycloaddition with the alkyne to form novel linearly fused tricyclic triazoles.
Download or read book Intramolecular Cyclization Strategies for Synthesizing Medium ring Polycycles and the Total Synthesis of Natural Products written by Dadasaheb V. Patil and published by . This book was released on 2012 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbo- and heterocyclic compounds are of great interest to chemists. Intramolecular cyclization strategies of donor-acceptor (D-A) cyclopropanes and alkylidene malonate monoamides have excellent potential for synthesis as they offer easy access to structurally-diverse compounds. The work described in this thesis accesses the scope of the In(OTf)3-catalyzed cyclization reaction of cyclopropanes and alkylidene malonate monoamides. In(OTf)3-catalyzed reactions of alkenyl and heteroaryl cyclopropyl ketones were examined in the synthesis of functionalized cyclohexenone-based derivatives (Chapter 2). Subsequent efforts to utilize a tandem cyclopropane ring-opening/Friedel-Crafts alkylation sequence of methyl 1-(1H-indolecarbonyl)-1-cyclopropanecarboxylates to prepare functionalized hydropyrido[1,2-a]indole-6(7H)-ones is discussed in Chapter 3. The extension of this tandem protocol towards the total synthesis of (±)-deethyleburnamonine is the subject of Chapter 6. Intramolecular Friedel-Crafts alkylation of N-indolyl alkylidene malonate monoamides was also examined. An In(OTf)3-catalyzed cyclization of substituted methyl 2-(1H-indole-1-carbonyl) acrylates afforded a series of 1H-pyrrolo[1,2-a]indole-3(2H)-ones (Chapter 4), whereas substrates with the indole 2-position blocked provided access to substituted 4H-pyrrolo[3,2,1-ij]quinolin-4-ones (Chapter 5).
Download or read book Artificial Metalloenzymes and MetalloDNAzymes in Catalysis written by Montserrat Diéguez and published by John Wiley & Sons. This book was released on 2018-02-21 with total page 431 pages. Available in PDF, EPUB and Kindle. Book excerpt: An important reference for researchers in the field of metal-enzyme hybrid catalysis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a comprehensive review of the most current strategies, developed over recent decades, for the design, synthesis, and optimization of these hybrid catalysts as well as material about their application. The contributors—noted experts in the field—present information on the preparation, characterization, and optimization of artificial metalloenzymes in a timely and authoritative manner. The authors present a thorough examination of this interesting new platform for catalysis that combines the excellent selective recognition/binding properties of enzymes with transition metal catalysts. The text includes information on the various applications of metal-enzyme hybrid catalysts for novel reactions, offers insights into the latest advances in the field, and contains an informative perspective on the future: Explores the development of artificial metalloenzymes, the modern and strongly evolving research field on the verge of industrial application Contains a comprehensive reference to the research area of metal-enzyme hybrid catalysis that has experienced tremendous growth in recent years Includes contributions from leading researchers in the field Shows how this new catalysis combines the selective recognition/binding properties of enzymes with transition metal catalysts Written for catalytic chemists, bioinorganic chemists, biochemists, and organic chemists, Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a unique reference to the fundamentals, concepts, applications, and the most recent developments for more efficient and sustainable synthesis.
Download or read book Applied Cross Coupling Reactions written by Yasushi Nishihara and published by Springer Science & Business Media. This book was released on 2012-12-14 with total page 247 pages. Available in PDF, EPUB and Kindle. Book excerpt: “Applied Cross-Coupling Reactions” provides students and teachers of advanced organic chemistry with an overview of the history, mechanisms and applications of cross-coupling reactions. Since the discovery of the transition-metal-catalyzed cross-coupling reactions in 1972, numerous synthetic uses and industrial applications have been developed. The mechanistic studies of the cross-coupling reactions have disclosed that three fundamental reactions: oxidative addition, transmetalation, and reductive elimination, are involved in a catalytic cycle. Cross-coupling reactions have allowed us to produce a variety of compounds for industrial purposes, such as natural products, pharmaceuticals, liquid crystals and conjugate polymers for use in electronic devices. Indeed, the Nobel Prize for Chemistry in 2010 was awarded for work on cross-coupling reactions. In this book, the recent trends in cross-coupling reactions are also introduced from the point of view of synthesis design and catalytic activities of transition-metal catalysts.
Download or read book C H Bond Activation and Catalytic Functionalization I written by Pierre H. Dixneuf and published by Springer. This book was released on 2015-12-18 with total page 269 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. In references, Topics in Organometallic Chemistry is abbreviated as Top Organomet Chem and cited as a journal.
Download or read book Hypervalent Iodine in Organic Synthesis written by A. Varvoglis and published by Academic Press. This book was released on 1996-11-14 with total page 245 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book describes the fascinating chemistry of the many kinds of organic compounds of hypervalent iodine. Each chapter deals with a particular iodine compound or families of compounds which have been used as reagents in a plethora of useful transformations. These include assorted oxidation, such as with the precious Dess-Martin reagent as well as with a wide range of further reactions. Prominent features of hypervalent iodine reagents derived from iodobenzene are: ready availability, operational simplicity, mild reaction conditions, and high efficiency. They are environmentally safe and can be recycled. New species may be easily prepared by introducing substituents in the benzene ring or changing the ligand attached to iodine. Their combination with other reagents broadens considerably their synthetic potential. Today, no synthetic chemist can afford to ignore the valuable hypervalentiodine reagents. - Features up-to-date coverage of a wide range of topics - Includes many tables featuring a diversity of reactivity, and a comprehensive index - Acts as a comprehensive, up-to-date reference on all aspects of hypervalent iodine chemistry - Contains a section on unusual efficiency of hypervalent iodine reactions
Download or read book Organic Synthesis written by Douglass F. Taber and published by Oxford University Press. This book was released on 2017 with total page 289 pages. Available in PDF, EPUB and Kindle. Book excerpt: A collection of Douglass Taber's columns originally published between 2013 - 2015 at www.organicchemistry.org
Download or read book Strategies and Solutions to Advanced Organic Reaction Mechanisms written by Andrei Hent and published by Academic Press. This book was released on 2019-06-28 with total page 886 pages. Available in PDF, EPUB and Kindle. Book excerpt: Strategies and Solutions to Advanced Organic Reaction Mechanisms: A New Perspective on McKillop's Problems builds upon Alexander (Sandy) McKillop's popular text, Solutions to McKillop's Advanced Problems in Organic Reaction Mechanisms, providing a unified methodological approach to dealing with problems of organic reaction mechanism. This unique book outlines the logic, experimental insight and problem-solving strategy approaches available when dealing with problems of organic reaction mechanism. These valuable methods emphasize a structured and widely applicable approach relevant for both students and experts in the field. By using the methods described, advanced students and researchers alike will be able to tackle problems in organic reaction mechanism, from the simple and straight forward to the advanced. - Provides strategic methods for solving advanced mechanistic problems and applies those techniques to the 300 original problems in the first publication - Replaces reliance on memorization with the understanding brought by pattern recognition to new problems - Supplements worked examples with synthesis strategy, green metrics analysis and novel research, where available, to help advanced students and researchers in choosing their next research project
Download or read book Stereoselective Synthesis written by Gary A. Molander and published by Thieme Chemistry. This book was released on 2011 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbonyl and imino groups are two of the most integral functional groups employed in organic synthesis. Specific topics discussed: reduction, alkylation, alkenylation, and arylation of these groups, as well as asymmetric aldol, Mannich, and Morita-Bayliss-Hillman reactions. This volume is part of a 3-volume set: Science of Synthesis Stereoselective Synthesis Workbench Edition Further information about Stereoselective Synthesis (including sample pages and the table of contents)
Download or read book Enzyme Engineering and Evolution General Methods written by and published by Academic Press. This book was released on 2020-09-05 with total page 362 pages. Available in PDF, EPUB and Kindle. Book excerpt: This new volume of Methods in Enzymology continues the legacy of this premier serial with quality chapters authored by leaders in the field. - Provides the authority and expertise of leading contributors from an international board of authors - Presents the latest release in the Methods in Enzymology series
Download or read book C C Bond Activation written by Guangbin Dong and published by Springer. This book was released on 2014-09-18 with total page 265 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience. Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students
