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Catalytic Enantioselective Synthesis Of Aryl Substituted 3 Hydroxy 2 Oxindoles And 33 Disubstituted 2 Oxindoles
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Book Synopsis Catalytic Enantioselective Synthesis of Aryl Substituted 3-hydroxy-2-oxindoles and 3,3-disubstituted-2-oxindoles by : Aziza Hatice Sahin
Download or read book Catalytic Enantioselective Synthesis of Aryl Substituted 3-hydroxy-2-oxindoles and 3,3-disubstituted-2-oxindoles written by Aziza Hatice Sahin and published by . This book was released on 2010 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: In Chapter One, a catalytic enantioselective method for the synthesis of 3- hydroxy-2-oxindoles is described. 3-Hydroxy-2-oxindoles were synthesized by a nucleophilic addition of electron-rich arenes and aromatic heterocycles to substituted indole-2,3-diones (isatins) catalyzed by scandium(III) and indium(III)-inda-pybox complexes. The use of a bulky chiral ligand hindered the formation of the achiral 3,3-diaryl-2-oxindole side product. Substituted 3-hydroxy-2-oxindoles were formed in high yield and high enantioselectivity (up to 99% ee). In Chapter Two, a method for the synthesis of chiral 3,3-disubstituted-2-oxindoles from a nucleophilic substitution at the stereocenter of a substituted 3-hydroxy-2-oxindole is described. This SN̳1-like process is catalyzed by a Lewis or a Brønsted acid, which eliminates water to form an indolenium ion intermediate. Chiral BINOL-derived phosphoric acids and phosphoramides are promising catalysts for an asymmetric process, as the conjugate base can act as a counteranion that coordinates to the carbocation intermediate to direct an asymmetric nucleophilic addition. Catalyst and solvent effects have been investigated with yields ranging from 68-97%. Preliminary enantioselectivity has been observed and further optimization is underway.
Book Synopsis Studies in Natural Products Chemistry by : Albert Moyano
Download or read book Studies in Natural Products Chemistry written by Albert Moyano and published by Elsevier Inc. Chapters. This book was released on 2013-06-25 with total page 83 pages. Available in PDF, EPUB and Kindle. Book excerpt: Functional diversity and molecular architecture in biologically active oxindoles. Transition metal-catalyzed intramolecular Heck reactions and amide alpha-arylations. Asymmetric rearrangements of O-carbonylated oxindoles and related processes. Amination, hydroxylation, and halogenation reactions of 3-substituted oxindoles. Conjugate addition and alkylation reactions of 3-substituted oxindoles. Asymmetric aldol and Mannich reactions of isatins. Michael additions to isatin-derived electron-deficient alkynes. Nucleophilic substitution reactions of functionalized 3-substituted oxindoles. Enantioselective construction of spirooxindoles by cycloaddition, annulation, and cascade cyclization reactions of methyleneindolinone derivatives. The 3,3-disubstituted-2-oxindole moiety is present in many chiral alkaloids that exhibit interesting biological activities. The enantioselective synthesis of chiral oxindole derivatives has been mainly achieved by asymmetric catalytic methods. In this review we highlight the most important catalytic methods relevant to the synthesis of chiral, non-spirocyclic 3,3-disubstituted oxindoles.
Book Synopsis Asymmetric Synthesis Of 3, 3-disubstituted Oxindoles by : Dalpozzo Renato
Download or read book Asymmetric Synthesis Of 3, 3-disubstituted Oxindoles written by Dalpozzo Renato and published by World Scientific. This book was released on 2019-09-11 with total page 320 pages. Available in PDF, EPUB and Kindle. Book excerpt: Indole derivatives are the most common heterocycle compounds present in nature, for this reason, they have been referred to as 'privileged structures'. In fact, many approved drugs — and natural products — belong to this family. Among indole derivatives, oxindoles have a structural complexity, which have stimulated generations of synthetic chemists to design strategies for assembling these structures, and their enantioselective synthesis is still growing.This book proposes to describe the known enantioselective syntheses of oxindole derivatives. It is divided in six chapters each referring to a specific class of asymmetric oxindole derivatives. After the introduction, Chapter 2 describes all-carbon spirooxindoles; Chapter 3, open chain 3,3-dialkyloxindoles; Chapter 4, 3-substituted-3-aminooxindoles; Chapter 5, 3-substituted-3-hydroxyoxindoles; Chapter 6, 3-hetero-3-substituted oxindoles. It will be a useful tool for synthetic chemists, who assemble total synthesis of natural products, as well as for drug discovery chemists either in academic or in industry R&S laboratories.
Book Synopsis Asymmetric Synthesis of 3, 3-disubstituted Oxindoles by : Renato Dalpozzo
Download or read book Asymmetric Synthesis of 3, 3-disubstituted Oxindoles written by Renato Dalpozzo and published by . This book was released on 2019 with total page 320 pages. Available in PDF, EPUB and Kindle. Book excerpt: "Indole derivatives are the most common heterocycle compounds present in nature, for this reason, they have been referred to as "privileged structures". In fact, many approved drugs - and natural products - belong to this family. Among indole derivatives, oxindoles have a structural complexity, which have stimulated generations of synthetic chemists to design strategies for assembling these structures, and their enantioselective synthesis is still growing. This book proposes to describe the known enantioselective syntheses of oxindole derivatives. It is divided in six chapters each referring to a specific class of asymmetric oxindole derivatives. After the introduction, Chapter 2 describes all-carbon spirooxindoles; Chapter 3, open chain 3,3-dialkyloxindoles; Chapter 4, 3-substituted-3-aminooxindoles; Chapter 5, 3-substituted-3-hydroxyoxindoles; Chapter 6, 3-hetero-3-substituted oxindoles. It will be a useful tool for synthetic chemists, who assemble total synthesis of natural products, as well as for drug discovery chemists either in academic or in industry R&S laboratories."--
Book Synopsis Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones Bearing a Quaternary Stereocenter and Reactions of Palladium Bisphosphine Complexes Relevant to Catalytic C-C Bond Formation by : Ivory Derrick Hills
Download or read book Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones Bearing a Quaternary Stereocenter and Reactions of Palladium Bisphosphine Complexes Relevant to Catalytic C-C Bond Formation written by Ivory Derrick Hills and published by . This book was released on 2004 with total page 376 pages. Available in PDF, EPUB and Kindle. Book excerpt: In Part I the development of a new method for the construction of oxindoles and benzofuranones bearing quaternary stereocenters is discussed. A planar-chiral PPY derivative catalyzes the O-to-C acyl group migration (Black rearrangement) in a highly efficient and enantioselective manner. The utility of this method is further demonstrated by the formal total synthesis of the natural product aplysin. In Part II reactivity of bisphosphine palladium-complexes is discussed. It is shown that the oxidative addition of bisphosphine palladium-complexes bearing P(t-Bu2)Me occurs through an SN2-type mechanism. This discovery allows us rationalize the difference in catalytic activity between Pd(P(t-Bu2)Me)2 and Pd(P(t-Bu2)Et)2 for the cross-coupling of alkyl electrophiles. The reductive elimination of H-X from bisphosphine palladium-hydride complexes is also discussed. The discovery that (P(t-Bu)3)2PdHCl undergoes facile reductive elimination in the presence of Cy2NMe, while (PCy3)2PdHCl does not, is explained using X-ray crystal structures. These reactivity patterns may help to explain why Pd(P(t-Bu)3)2 is a much better catalyst than Pd(PCy3)2 for the Heck coupling of aryl chlorides. Finally, Part III describes preliminary work on a palladium-hydride catalyzed isomerization of allylic alcohols as well as initial attempts to study the mechanism of nickel-catalyzed cross-couplings of secondary alkyl-electrophiles.
Book Synopsis Scandium(III)- and Indium(III)-catalyzed Enantioselective Additions to Isatin for the Synthesis of 3-hydroxy-2-oxindoles and [(3'-trialkylsilyl)-tetrahydrofuranyl]spirooxindoles by : Nadine Victor Hanhan
Download or read book Scandium(III)- and Indium(III)-catalyzed Enantioselective Additions to Isatin for the Synthesis of 3-hydroxy-2-oxindoles and [(3'-trialkylsilyl)-tetrahydrofuranyl]spirooxindoles written by Nadine Victor Hanhan and published by . This book was released on 2013 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The enantioselective synthesis of oxindole products is desirable, for they comprise an important structural motif of various natural products, complex bioactive molecules, andpharmaceutical lead compounds. This dissertation presents the development of efficient andhighly enantioselective methods for the synthesis of 3-substituted-3-hydroxy-2-oxindoles and 3-spirocyclic-2-oxindoles. These efficient and operationally simple methods generate oxindoleproducts from direct additions of π-nucleophiles to isatins. Chapter one provides a summary of literature that highlights strategies for the catalyticasymmetric synthesis of 3-hydroxy-2-oxindoles, spirocyclic oxindoles, and other spirocycliccompounds. The notable spirocyclization examples presented are focused on strategies thatcreate a spirocenter within the key step of a catalytic asymmetric process. Chapter two describes my strategy for the development of the first catalytic asymmetricand direct addition of π-nucleophiles to isatin electrophiles for the synthesis of biologically relevant substituted 3-hydroxy-2-oxindoles. This chapter demonstrates the first example of anenantioselective scandium(III)- and indium(III)-pybox catalyzed addition of indoles, otherelectron rich arenes, silyl enol ethers, and allylstannanes to both N-alkylated and NH isatins.The chapter provides a comparison of reactivity and enantioselectivity of metal complexes in the nucleophilic addition to isatin. It specifically describes the ability of these catalysts to suppress the formation of the 3,3-diaryloxindole product while facilitating the enantioselective synthesis of 3-indolyl-3-hydroxy-2-oxindoles. Chapter three presents the development of a scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes. Catalyst loading as low as 0.05 mol % can be utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application of this reaction. Chapter four describes the discovery and development of the first catalytic asymmetric [3+2] allylsilane annulation reaction, allowing for the enantioselective synthesis of silyl and hydroxy spirooxindoles. The method for this annulation reaction utilizes a chiral ScCl2(SbF6)-indapybox complex with TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity (99% ee) at room temperature.
Book Synopsis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis by : Montserrat Diéguez
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.
Book Synopsis Catalytic Arylation Methods by : Anthony J. Burke
Download or read book Catalytic Arylation Methods written by Anthony J. Burke and published by John Wiley & Sons. This book was released on 2015-02-09 with total page 530 pages. Available in PDF, EPUB and Kindle. Book excerpt: This "hands-on" approach to the topic of arylation consolidates the body of key research over the last ten years (and up to around 2014) on various catalytic methods which involve an arylation process. Clearly structured, the chapters in this one-stop resource are arranged according to the reaction type, and focus on novel, efficient and sustainable processes, rather than the well-known and established cross-coupling methods. The entire contents are written by two authors with academic and industrial expertise to ensure consistent coverage of the latest developments in the field, as well as industrial applications, such as C-H activation, iron and gold-catalyzed coupling reactions, cycloadditions or novel methodologies using arylboron reagents. A cross-section of relevant tried-and-tested experimental protocols is included at the end of each chapter for putting into immediate practice, along with patent literature. Due to its emphasis on efficient, "green" methods and industrial applications of the products concerned, this interdisciplinary text will be essential reading for synthetic chemists in both academia and industry, especially in medicinal and process chemistry.
Book Synopsis Rhodium-Catalyzed Enantioselective Desymmetrizations of Oxabicyclic Alkenes and Alkene Difunctionalization Via Nickel-Catalyzed Arylcyanation by : Andy Wei Jen Yen
Download or read book Rhodium-Catalyzed Enantioselective Desymmetrizations of Oxabicyclic Alkenes and Alkene Difunctionalization Via Nickel-Catalyzed Arylcyanation written by Andy Wei Jen Yen and published by . This book was released on 2020 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: The synthesis of heterocycles using transition metal catalysis is a topic of broad interest in the field of organic chemistry. Transition metal catalysts allow many diverse bond disconnections to be realized, allowing for many ways to assemble heterocycles. Many of the transformations developed in the Lautens group are aimed at atom economical bond construction processes that streamline synthesis and minimize waste. The arylcyanation reaction and the asymmetric ring opening (ARO) reaction are two examples of methods developed in our group that embody this design principle. Chapter 1 of this thesis describes the development of a nickel-catalyzed arylcyanation reaction for the synthesis of 3,3-disubstituted oxindoles. This method was inspired by our work on the palladium-catalyzed arylcyanation reaction, originally developed to address challenges in the formal synthesis of (+)-corynoline. This nickel-catalyzed reaction uses an air-stable catalyst precursor to achieve a highly practical synthesis of a nitrile-containing oxindole via a domino Heck-cyanide capture cascade. Derivatizations of the nitrile group affords a series of novel heterocyclic scaffolds. Chapter 2 details the discovery and development of a novel enantioselective cycloisomerization reaction of oxabicyclic alkenes. Our work on developing the intramolecular asymmetric ring opening reaction led to the discovery of a novel epoxide synthesis. Specifically, when bridgehead substituted oxabicyclic alkenes with non-nucleophilic side chains are reacted with the [Rh(cod)2]OTf/PPF-PtBu2 catalyst in the absence of an external nucleophile, chiral epoxides are obtained. The synthesis of epoxides through cycloisomerization reactions possesses 100% atom economy and avoids the use of external oxidant. Chapter 3 describes an asymmetric ring opening reaction, specifically to address gaps in the methodology concerning amine nucleophiles. We were inspired by our group's previous attempts to use amino acid derived nucleophiles in the ARO reaction. We developed a way to incorporate amino acids into the ARO reaction by employing their 2-nitrobenzenesulfonamide (nosyl) derivatives as pronucleophiles. Intriguingly, we observed a divergence in reactivity between the diastereomeric hydroxyester products, in that one diastereomer was capable of lactonization and the other was not. This led to the enantioselective synthesis of chiral oxazinones, which are similar to the naphthoxazine class of compounds which possess dopaminergic activity.
Book Synopsis Chiral Lewis Acid and Organocatalytic Methods for the Asymmetric Synthesis and Functionalization of 3,3'-oxindoles and 3,3'-spirocyclic Oxindoles by : Joseph Jesse Badillo
Download or read book Chiral Lewis Acid and Organocatalytic Methods for the Asymmetric Synthesis and Functionalization of 3,3'-oxindoles and 3,3'-spirocyclic Oxindoles written by Joseph Jesse Badillo and published by . This book was released on 2014 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The development of regio- and stereoselective methods for the synthesis of oxindoles and spirocyclic oxindoles is important due to the prevalence of these structures in natural products and medicinal agents. This dissertation describes both Lewis acid and organocatalytic strategies for the regio-, diastereo-, and enantioselective synthesis of several classes of 3,3'-oxindoles and 3,3'-spirooxindoles. These strategies are applied to several synthetic transformations including allylsilane annulations, Friedel-Crafts alkylations, and Pictet-Spengler reactions. Chapter one describes an overview of recent methods for the enantioselective synthesis of oxindoles and spirooxindoles with a particular focus on scaffolds relevant to drug discovery. This overview is organized by type of catalyst and strategy in order to compare traditional organometallic and Lewis acid methods with recent organocatalytic methods. This chapter also features a section on multicomponent and cascade reaction strategies. Chapter two describes the development of synthetic methodology using titanium(IV)-catalysis for the selective synthesis of two new classes of spirocyclic oxindoles. In the first section, I present a highly regio- and diastereoselective method for the synthesis of spiro[3,3'oxindoleoxazolines] upon addition of 5-methoxy-2-oxazoles to isatins. In the second section, I present a method for the addition of 5-methoxy-2-aryloxazoles to [alpha],[beta]-unsaturated alkylidene oxindoles to provide access to spiro[3,3'oxindole-1-pyrrolines] with excellent yields and diastereoselectivities. This methodology is also effective for the diastereoselective synthesis of 1-pyrrolines derived from coumarins and simple malonates. Chapter three describes the condensation cyclization between isatins and 5-methoxytryptamine catalyzed by chiral phosphoric acids to provide spirooxindole tetrahydro-[beta]-carboline products in excellent yields and enantioselectivity. A comparison of catalysts provides insight for the reaction scope and factors responsible for efficient catalytic activity and selectivity in these Pictet-Spengler type spirocyclization reactions. In addition I show that chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration. Chapter four describes a strategy for the efficient two-step synthesis of triazole derivatives of oxindoles and spirooxindoles. Using a common set of N-propargylated isatins, a series of mechanistically distinct stereoselective reactions with different combinations of nucleophiles and catalysts provides access to diverse hydroxy-oxindoles, spiroindolones, and spirocyclic oxazoline structures. The resulting N-propargylated oxindoles are then converted to triazoles using copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. This strategy is used for the synthesis of a 64-member pilot-scale library of diverse oxindoles and spirooxindoles. Chapter five describes the first catalytic asymmetric [3+2] allylsilane annulation for the synthesis of cyclopentanes containing an all-carbon quaternary spirocenter. The annulation reaction is catalyzed with a chiral scandium(III)-indapybox complex where a sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaBArF) anion is essential for catalytic activity and stereoselectivity. Lactone formation affords evidence for an ester stabilized [beta]-silyl carbocation. Further transformations provide access to N-H spirooxindoles and allow transformation of the silyl group to a hydroxyl moiety. This catalyst complex is also effective for the asymmetric Friedel-Crafts conjugate addition of variety of additional pi-nucleophiles (i.e. indoles, pyrroles, anilines) to [alpha],[beta]-unsaturated alkylidene oxindoles. This methodology is also effective for the diastereoselective synthesis of coumarin and simple malonate derivatives.
Book Synopsis Copper-Catalyzed Electrophilic Amination of sp2 and sp3 C−H Bonds by : Stacey L. McDonald
Download or read book Copper-Catalyzed Electrophilic Amination of sp2 and sp3 C−H Bonds written by Stacey L. McDonald and published by Springer. This book was released on 2016-08-18 with total page 162 pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis reports the latest developments in the direct amination of various C−H bonds using an H−Zn exchange/electrophilic amination strategy. McDonald and co-workers reveal this approach to be a rapid and powerful method for accessing a variety of functionalized amines. The material outlined in this book shows how McDonald achieved C−H zincation using strong, non-nucleophilic zinc bases and subsequent electrophilic amination of the corresponding zinc carbanions with copper as a catalyst and O-benzoylhydroxylamines as the electrophilic nitrogen source. McDonald’s findings are of relevance to medicinal chemistry, drug discovery and materials science. Her thesis is a source of inspiration for scientists entering the field and students beginning their PhD in a related area.
Book Synopsis 1. Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation, 2. Double Cross-coupling Reactions of Siloxaborolates, 3. The Enantioselective Synthesis of 3-substituted Morpholines Using Computer-guided Catalyst Design by : Nessa Carson
Download or read book 1. Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation, 2. Double Cross-coupling Reactions of Siloxaborolates, 3. The Enantioselective Synthesis of 3-substituted Morpholines Using Computer-guided Catalyst Design written by Nessa Carson and published by . This book was released on 2016 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Inventing Reactions by : Lukas J. Gooßen
Download or read book Inventing Reactions written by Lukas J. Gooßen and published by Springer. This book was released on 2012-10-30 with total page 345 pages. Available in PDF, EPUB and Kindle. Book excerpt: Barry Trost: Transition metal catalyzed allylic alkylation.- Jeffrey W. Bode: Reinventing Amide Bond Formation.- Naoto Chatani and Mamoru Tobisu: Catalytic Transformations Involving the Cleavage of C-OMe Bonds.- Gregory L. Beutner and Scott E. Denmark: The Interplay of Invention, Observation and Discovery in the Development of Lewis Base Activation of Lewis Acids for Catalytic Enantioselective Synthesis.- David R. Stuart and Keith Fagnou: The Discovery and Development of a Palladium(II)-Catalyzed Oxidative Cross-Coupling of Two Unactivated Arenes.- Lukas Gooßen and Käthe Gooßen: Decarboxylative Cross-Coupling Reactions.- A. Stephen K. Hashmi: Gold-Catalyzed Organic Reactions.- Ben List: Developing Catalytic Asymmetric Acetalizations.- Steven M. Bischof, Brian G. Hashiguchi, Michael M. Konnick, and Roy A. Periana: The De NovoDesign of CH Bond Hydroxylation Catalysts.- Benoit Cardinal-David, Karl A. Scheidt: Carbene Catalysis: Beyond the Benzoin and Stetter Reactions.- Kenso Soai and Tsuneomi Kawasaki: Asymmetric autocatalysis of pyrimidyl alkanol.- Douglas C. Behenna and Brian M. Stoltz: Natural Products as Inspiration for Reaction Development: Catalytic Enantioselective Decarboxylative Reactions of Prochiral Enolate Equivalents. Hisashi Yamamoto: Acid Catalysis in Organic Synthesis.
Book Synopsis Synthesis of 4- to 7-membered Heterocycles by Ring Expansion by : Matthias D’hooghe
Download or read book Synthesis of 4- to 7-membered Heterocycles by Ring Expansion written by Matthias D’hooghe and published by Springer. This book was released on 2015-12-14 with total page 376 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal.
Book Synopsis Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons by : Jun Yang
Download or read book Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons written by Jun Yang and published by OAE Publishing Inc.. This book was released on 2023-02-08 with total page 54 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chiral spirolactones, including spiropropyllactones, spirobutyrolactones, and spirovalerolactones, are important heterocyclic frameworks that attracted the attention of organic and medicinal chemists because these motifs constitute the core structure of several natural products and bioactive molecules. The absolute configuration and the substituents on the fully substituted spirocyclic stereocenter of the lactone can potentially enhance specificity for ligand-protein binding and enhance bioavailability, potency, and metabolic stability. So, intensive attention from chemists has been paid to the synthetic methods leading to such prominent structural motifs. The synthetic methods can be divided into two main classes. The first approach takes advantage of the presence of the existing lactone structure and focuses on its functionalization. The second approach is the lactone framework constructed from various precursors in a direct spirolactonization reaction. In this review, for convenience in reading, the recent advances in the synthesis of spirolactones are summarized and discussed according to the two major organocatalytic asymmetric synthetic routes: (i) using the lactone-related frameworks as building blocks; and (ii) direct spirolactonization reaction using various reagents. This review also describes both the mechanisms and related transformations, and gives some insights into challenging issues in this research field, which will enlighten the future development of this field.
Book Synopsis Alkaline-Earth Metal Compounds by : Sjoerd Harder
Download or read book Alkaline-Earth Metal Compounds written by Sjoerd Harder and published by Springer. This book was released on 2013-07-20 with total page 282 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 in 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.
Book Synopsis N-Heterocyclic Carbenes in Organocatalysis by : Akkattu T. Biju
Download or read book N-Heterocyclic Carbenes in Organocatalysis written by Akkattu T. Biju and published by John Wiley & Sons. This book was released on 2019-01-07 with total page 407 pages. Available in PDF, EPUB and Kindle. Book excerpt: Summarizing the emerging field of N-heterocyclic carbenes used in organocatalysis, this is an excellent overview of the synthesis and applications of NHCs focusing on carbon-carbon and carbon-heteroatom bond formation. Alongside comprehensive coverage of the synthesis, characteristics and applications, this handbook and ready reference also includes chapters on NHCs for polymerization reactions and natural product synthesis.
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