Synthesis of Biaryls

Synthesis of Biaryls

Author: Ivica Cepanec

Publisher: Elsevier

Published: 2010-07-07

Total Pages: 365

ISBN-13: 0080474535

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Organic chemistry is one of the most rapidly growing sciences. There is a wide variety of applications of organic compounds, for instance, pharmaceutically active substances, agrochemicals, optoelectronics, etc. Within this group there are hundereds and thousands of new compounds synthesized or isolated from natural sources. Such important organic chemistry developments are accompanied by the profound break-through of new reactions, increasingly efficient methodologies, reagents and catalysts. The chemistry of biaryls is one of the most interesting fields in organic chemistry, this book looks at these reactions both new and old. Synthesis of Biaryls presents the description of a given method for the synthesis of biaryls: short introduction, reaction mechanism, application, representative synthetic procedures, conclusion and literature references. This book will be of interest to organic chemists in industry and academia. A topic of growing importance in organic synthesis The FIRST book to cover all reactions for the synthesis of biaryls, including the most recent The book provides detailed applications of each method described


Book Synopsis Synthesis of Biaryls by : Ivica Cepanec

Download or read book Synthesis of Biaryls written by Ivica Cepanec and published by Elsevier. This book was released on 2010-07-07 with total page 365 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organic chemistry is one of the most rapidly growing sciences. There is a wide variety of applications of organic compounds, for instance, pharmaceutically active substances, agrochemicals, optoelectronics, etc. Within this group there are hundereds and thousands of new compounds synthesized or isolated from natural sources. Such important organic chemistry developments are accompanied by the profound break-through of new reactions, increasingly efficient methodologies, reagents and catalysts. The chemistry of biaryls is one of the most interesting fields in organic chemistry, this book looks at these reactions both new and old. Synthesis of Biaryls presents the description of a given method for the synthesis of biaryls: short introduction, reaction mechanism, application, representative synthetic procedures, conclusion and literature references. This book will be of interest to organic chemists in industry and academia. A topic of growing importance in organic synthesis The FIRST book to cover all reactions for the synthesis of biaryls, including the most recent The book provides detailed applications of each method described

Axially Chiral Compounds

Axially Chiral Compounds

Author: Bin Tan

Publisher: John Wiley & Sons

Published: 2021-11-22

Total Pages: 338

ISBN-13: 3527347127

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Axially Chiral Compounds Explore this comprehensive and current volume summarizing the characteristics, synthesis, and applications of axial chirality Appearing widely in natural products, biologically active molecules, asymmetric chemistry, and material science, axially chiral motifs constitute the core backbones of the majority of chiral ligands and organocatalysts in asymmetric catalysis. In a new work of particular relevance to synthetic chemists, Axially Chiral Compounds: Asymmetric Synthesis and Applications delivers a clearly structured and authoritative volume covering the classification, characteristics, synthesis, and applications of axial chirality. A must read for every synthetic chemist practicing today, the book follows the development history, research status, and applications of axial chirality. An introductory chapter familiarizes the reader with foundational material before the distinguished authors describe the different classes and the synthesis of axial chiral compounds used in asymmetric synthesis. The book concludes with a focus on the applications of chiral ligands, chiral catalysts, and materials. Readers will also benefit from the inclusion of: A thorough introduction to asymmetric synthesis, including biaryls atropisomers, heterobiaryls atropisomers, and non-biaryls atropisomers Explorations of chiral allene, spiro skeletons, and natural products Practical discussions of asymmetric transformation, chiral ligands, and chiral catalysts An examination of miscellaneous applications of axially chiral compounds Perfect for organic chemists, chemists working with or on organometallics, catalytic chemists, and materials scientists, Axially Chiral Compounds: Asymmetric Synthesis and Applications will also earn a place in the libraries of natural products chemists who seek a one-stop reference for compounds exhibiting axial chirality.


Book Synopsis Axially Chiral Compounds by : Bin Tan

Download or read book Axially Chiral Compounds written by Bin Tan and published by John Wiley & Sons. This book was released on 2021-11-22 with total page 338 pages. Available in PDF, EPUB and Kindle. Book excerpt: Axially Chiral Compounds Explore this comprehensive and current volume summarizing the characteristics, synthesis, and applications of axial chirality Appearing widely in natural products, biologically active molecules, asymmetric chemistry, and material science, axially chiral motifs constitute the core backbones of the majority of chiral ligands and organocatalysts in asymmetric catalysis. In a new work of particular relevance to synthetic chemists, Axially Chiral Compounds: Asymmetric Synthesis and Applications delivers a clearly structured and authoritative volume covering the classification, characteristics, synthesis, and applications of axial chirality. A must read for every synthetic chemist practicing today, the book follows the development history, research status, and applications of axial chirality. An introductory chapter familiarizes the reader with foundational material before the distinguished authors describe the different classes and the synthesis of axial chiral compounds used in asymmetric synthesis. The book concludes with a focus on the applications of chiral ligands, chiral catalysts, and materials. Readers will also benefit from the inclusion of: A thorough introduction to asymmetric synthesis, including biaryls atropisomers, heterobiaryls atropisomers, and non-biaryls atropisomers Explorations of chiral allene, spiro skeletons, and natural products Practical discussions of asymmetric transformation, chiral ligands, and chiral catalysts An examination of miscellaneous applications of axially chiral compounds Perfect for organic chemists, chemists working with or on organometallics, catalytic chemists, and materials scientists, Axially Chiral Compounds: Asymmetric Synthesis and Applications will also earn a place in the libraries of natural products chemists who seek a one-stop reference for compounds exhibiting axial chirality.

Privileged Structures in Drug Discovery

Privileged Structures in Drug Discovery

Author: Larry Yet

Publisher: John Wiley & Sons

Published: 2018-03-07

Total Pages: 560

ISBN-13: 1118686357

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A comprehensive guide to privileged structures and their application in the discovery of new drugs The use of privileged structures is a viable strategy in the discovery of new medicines at the lead optimization stages of the drug discovery process. Privileged Structures in Drug Discovery offers a comprehensive text that reviews privileged structures from the point of view of medicinal chemistry and contains the synthetic routes to these structures. In this text, the author—a noted expert in the field—includes an historical perspective on the topic, presents a practical compendium to privileged structures, and offers an informed perspective on the future direction for the field. The book describes the up-to-date and state-of-the-art methods of organic synthesis that describe the use of privileged structures that are of most interest. Chapters included information on benzodiazepines, 1,4-dihydropyridines, biaryls, 4-(hetero)arylpiperidines, spiropiperidines, 2-aminopyrimidines, 2-aminothiazoles, 2-(hetero)arylindoles, tetrahydroisoquinolines, 2,2-dimethylbenzopyrans, hydroxamates, and bicyclic pyridines containing ring-junction nitrogen as privileged scaffolds in medicinal chemistry. Numerous, illustrative case studies document the current use of the privileged structures in the discovery of drugs. This important volume: Describes the drug compounds that have successfully made it to the marketplace and the chemistry associated with them Offers the experience from an author who has worked in many therapeutic areas of medicinal chemistry Details many of the recent developments in organic chemistry that prepare target molecules Includes a wealth of medicinal chemistry case studies that clearly illustrate the use of privileged structures Designed for use by industrial medicinal chemists and process chemists, academic organic and medicinal chemists, as well as chemistry students and faculty, Privileged Structures in Drug Discovery offers a current guide to organic synthesis methods to access the privileged structures of interest, and contains medicinal chemistry case studies that document their application.


Book Synopsis Privileged Structures in Drug Discovery by : Larry Yet

Download or read book Privileged Structures in Drug Discovery written by Larry Yet and published by John Wiley & Sons. This book was released on 2018-03-07 with total page 560 pages. Available in PDF, EPUB and Kindle. Book excerpt: A comprehensive guide to privileged structures and their application in the discovery of new drugs The use of privileged structures is a viable strategy in the discovery of new medicines at the lead optimization stages of the drug discovery process. Privileged Structures in Drug Discovery offers a comprehensive text that reviews privileged structures from the point of view of medicinal chemistry and contains the synthetic routes to these structures. In this text, the author—a noted expert in the field—includes an historical perspective on the topic, presents a practical compendium to privileged structures, and offers an informed perspective on the future direction for the field. The book describes the up-to-date and state-of-the-art methods of organic synthesis that describe the use of privileged structures that are of most interest. Chapters included information on benzodiazepines, 1,4-dihydropyridines, biaryls, 4-(hetero)arylpiperidines, spiropiperidines, 2-aminopyrimidines, 2-aminothiazoles, 2-(hetero)arylindoles, tetrahydroisoquinolines, 2,2-dimethylbenzopyrans, hydroxamates, and bicyclic pyridines containing ring-junction nitrogen as privileged scaffolds in medicinal chemistry. Numerous, illustrative case studies document the current use of the privileged structures in the discovery of drugs. This important volume: Describes the drug compounds that have successfully made it to the marketplace and the chemistry associated with them Offers the experience from an author who has worked in many therapeutic areas of medicinal chemistry Details many of the recent developments in organic chemistry that prepare target molecules Includes a wealth of medicinal chemistry case studies that clearly illustrate the use of privileged structures Designed for use by industrial medicinal chemists and process chemists, academic organic and medicinal chemists, as well as chemistry students and faculty, Privileged Structures in Drug Discovery offers a current guide to organic synthesis methods to access the privileged structures of interest, and contains medicinal chemistry case studies that document their application.

The Ullmann Synthesis in Relation to the Preparation of Biaryls

The Ullmann Synthesis in Relation to the Preparation of Biaryls

Author: Harold Donald Willard

Publisher:

Published: 1953

Total Pages: 98

ISBN-13:

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Book Synopsis The Ullmann Synthesis in Relation to the Preparation of Biaryls by : Harold Donald Willard

Download or read book The Ullmann Synthesis in Relation to the Preparation of Biaryls written by Harold Donald Willard and published by . This book was released on 1953 with total page 98 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Nickel Catalysis in Organic Synthesis

Nickel Catalysis in Organic Synthesis

Author: Sensuke Ogoshi

Publisher: John Wiley & Sons

Published: 2020-03-09

Total Pages: 348

ISBN-13: 3527344071

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A comprehensive reference to nickel chemistry for every scientist working with organometallic catalysts Written by one of the world?s leading reseachers in the field, Nickel Catalysis in Organic Synthesis presents a comprehensive review of the high potential of modern nickel catalysis and its application in synthesis. Structured in a clear and assessible manner, the book offers a collection of various reaction types, such as cross-coupling reactions, reactions for the activation of unreactive bonds, carbon dioxide fixation, and many more. Nickel has been recognized as one of the most interesting transition metals for homogeneous catalysis. This book offers an overview to the recently developed new ligands, new reaction conditions, and new apparatus to control the reactivity of nickel catalysts, allowing scientists to apply nickel catalysts to a variety of bond-forming reactions. A must-read for anyone working with organometallic compounds and their application in organic synthesis, this important guide: -Reviews the numerous applications of nickel catalysis in synthesis -Explores the use of nickel as a relatively cheap and earth-abundant metal -Examines the versatility of nickel catalysis in reactions like cross-coupling reactions and CH activations -Offers a resource for academics and industry professionals Written for catalytic chemists, organic chemists, inorganic chemists, structural chemists, and chemists in industry, Nickel Catalysis in Organic Synthesis provides a much-needed overview of the most recent developments in modern nickel catalysis and its application in synthesis.


Book Synopsis Nickel Catalysis in Organic Synthesis by : Sensuke Ogoshi

Download or read book Nickel Catalysis in Organic Synthesis written by Sensuke Ogoshi and published by John Wiley & Sons. This book was released on 2020-03-09 with total page 348 pages. Available in PDF, EPUB and Kindle. Book excerpt: A comprehensive reference to nickel chemistry for every scientist working with organometallic catalysts Written by one of the world?s leading reseachers in the field, Nickel Catalysis in Organic Synthesis presents a comprehensive review of the high potential of modern nickel catalysis and its application in synthesis. Structured in a clear and assessible manner, the book offers a collection of various reaction types, such as cross-coupling reactions, reactions for the activation of unreactive bonds, carbon dioxide fixation, and many more. Nickel has been recognized as one of the most interesting transition metals for homogeneous catalysis. This book offers an overview to the recently developed new ligands, new reaction conditions, and new apparatus to control the reactivity of nickel catalysts, allowing scientists to apply nickel catalysts to a variety of bond-forming reactions. A must-read for anyone working with organometallic compounds and their application in organic synthesis, this important guide: -Reviews the numerous applications of nickel catalysis in synthesis -Explores the use of nickel as a relatively cheap and earth-abundant metal -Examines the versatility of nickel catalysis in reactions like cross-coupling reactions and CH activations -Offers a resource for academics and industry professionals Written for catalytic chemists, organic chemists, inorganic chemists, structural chemists, and chemists in industry, Nickel Catalysis in Organic Synthesis provides a much-needed overview of the most recent developments in modern nickel catalysis and its application in synthesis.

Synthesis of Heterocycles and Biaryls Via Anion-accelerated Palladium-mediated Coupling Reactions

Synthesis of Heterocycles and Biaryls Via Anion-accelerated Palladium-mediated Coupling Reactions

Author: Del David Hennings

Publisher:

Published: 1997

Total Pages: 564

ISBN-13:

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Book Synopsis Synthesis of Heterocycles and Biaryls Via Anion-accelerated Palladium-mediated Coupling Reactions by : Del David Hennings

Download or read book Synthesis of Heterocycles and Biaryls Via Anion-accelerated Palladium-mediated Coupling Reactions written by Del David Hennings and published by . This book was released on 1997 with total page 564 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Transition-Metal-Mediated Aromatic Ring Construction

Transition-Metal-Mediated Aromatic Ring Construction

Author: Ken Tanaka

Publisher: John Wiley & Sons

Published: 2013-07-09

Total Pages: 785

ISBN-13: 111862999X

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State-of-the-science methods, synthetic routes, and strategies to construct aromatic rings The development of new reactions for the synthesis of aromatic compounds is a highly active research area in organic synthesis, providing new functional organic materials, functional reagents, and biologically active compounds. Recently, significant advances in transition-metal-mediated reactions have enabled the efficient and practical construction of new aromatic rings with useful properties and applications. This book draws together and reviews all the latest discoveries and methods in transition-metal-mediated reactions, offering readers promising new routes to design and construct complex aromatic compounds. Integrating metal catalysis with aromatic compound synthesis, Transition-Metal-Mediated Aromatic Ring Construction offers a practical guide to the methods, synthetic routes, and strategies for constructing aromatic compounds. The book's five parts examine: [2+2+2], [2+2+1], and related cycloaddition reactions [4+2], [3+2], and related cycloaddition reactions Electrocyclization reactions Coupling and addition reactions Other important transformations, including methathesis reactions and skeletal rearrangement reactions Edited by Ken Tanaka, an internationally recognized expert in the field of transition-metal catalysis, the book features authors who are leading pioneers and researchers in synthetic reactions. Their contributions reflect a thorough review and analysis of the literature as well as their own firsthand laboratory experience developing new aromatic compounds. All chapters end with a summary and outlook, setting forth new avenues of research and forecasting new discoveries. There are also references at the end of each chapter, guiding readers to important original research reports and reviews. In summary, Transition-Metal-Mediated Aromatic Ring Construction offers synthetic chemists a promising new avenue for the development of important new aromatic compounds with a broad range of applications.


Book Synopsis Transition-Metal-Mediated Aromatic Ring Construction by : Ken Tanaka

Download or read book Transition-Metal-Mediated Aromatic Ring Construction written by Ken Tanaka and published by John Wiley & Sons. This book was released on 2013-07-09 with total page 785 pages. Available in PDF, EPUB and Kindle. Book excerpt: State-of-the-science methods, synthetic routes, and strategies to construct aromatic rings The development of new reactions for the synthesis of aromatic compounds is a highly active research area in organic synthesis, providing new functional organic materials, functional reagents, and biologically active compounds. Recently, significant advances in transition-metal-mediated reactions have enabled the efficient and practical construction of new aromatic rings with useful properties and applications. This book draws together and reviews all the latest discoveries and methods in transition-metal-mediated reactions, offering readers promising new routes to design and construct complex aromatic compounds. Integrating metal catalysis with aromatic compound synthesis, Transition-Metal-Mediated Aromatic Ring Construction offers a practical guide to the methods, synthetic routes, and strategies for constructing aromatic compounds. The book's five parts examine: [2+2+2], [2+2+1], and related cycloaddition reactions [4+2], [3+2], and related cycloaddition reactions Electrocyclization reactions Coupling and addition reactions Other important transformations, including methathesis reactions and skeletal rearrangement reactions Edited by Ken Tanaka, an internationally recognized expert in the field of transition-metal catalysis, the book features authors who are leading pioneers and researchers in synthetic reactions. Their contributions reflect a thorough review and analysis of the literature as well as their own firsthand laboratory experience developing new aromatic compounds. All chapters end with a summary and outlook, setting forth new avenues of research and forecasting new discoveries. There are also references at the end of each chapter, guiding readers to important original research reports and reviews. In summary, Transition-Metal-Mediated Aromatic Ring Construction offers synthetic chemists a promising new avenue for the development of important new aromatic compounds with a broad range of applications.

C-H Activation for Asymmetric Synthesis

C-H Activation for Asymmetric Synthesis

Author: Françoise Colobert

Publisher: John Wiley & Sons

Published: 2019-11-11

Total Pages: 294

ISBN-13: 3527343407

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Provides, in one handbook, comprehensive coverage of one of the hottest topics in stereoselective chemistry Written by leading international authors in the field, this book introduces readers to C-H activation in asymmetric synthesis along with all of its facets. It presents stereoselective C-H functionalization with a broad coverage, from outer-sphere to inner-sphere C-H bond activation, and from the control of olefin geometry to the induction of point, planar and axial chirality. Moreover, methods wherein asymmetry is introduced either during the C-H activation or in a different elementary step are discussed. Presented in two parts?asymmetric activation of C(sp3)-H bonds and stereoselective synthesis implying activation of C(sp2)-H bonds?CH-Activation for Asymmetric Synthesis showcases the diversity of stereogenic elements, which can now be constructed by C-H activation methods. Chapters in Part 1 cover: C(sp3)-H bond insertion by metal carbenoids and nitrenoids; stereoselective C-C bond and C-N bond forming reactions through C(sp3)?H bond insertion of metal nitrenoids; enantioselective intra- and intermolecular couplings; and more. Part 2 looks at: C-H activation involved in stereodiscriminant step; planar chirality; diastereoselective formation of alkenes through C(sp2)?H bond activation; amongst other methods. -Covers one of the most rapidly developing fields in organic synthesis and catalysis -Clearly structured in two parts (activation of sp3- and activation of sp2-H bonds) -Edited by two leading experts in C-H activation in asymmetric synthesis CH-Activation for Asymmetric Synthesis will be of high interest to chemists in academia, as well as those in the pharmaceutical and agrochemical industry.


Book Synopsis C-H Activation for Asymmetric Synthesis by : Françoise Colobert

Download or read book C-H Activation for Asymmetric Synthesis written by Françoise Colobert and published by John Wiley & Sons. This book was released on 2019-11-11 with total page 294 pages. Available in PDF, EPUB and Kindle. Book excerpt: Provides, in one handbook, comprehensive coverage of one of the hottest topics in stereoselective chemistry Written by leading international authors in the field, this book introduces readers to C-H activation in asymmetric synthesis along with all of its facets. It presents stereoselective C-H functionalization with a broad coverage, from outer-sphere to inner-sphere C-H bond activation, and from the control of olefin geometry to the induction of point, planar and axial chirality. Moreover, methods wherein asymmetry is introduced either during the C-H activation or in a different elementary step are discussed. Presented in two parts?asymmetric activation of C(sp3)-H bonds and stereoselective synthesis implying activation of C(sp2)-H bonds?CH-Activation for Asymmetric Synthesis showcases the diversity of stereogenic elements, which can now be constructed by C-H activation methods. Chapters in Part 1 cover: C(sp3)-H bond insertion by metal carbenoids and nitrenoids; stereoselective C-C bond and C-N bond forming reactions through C(sp3)?H bond insertion of metal nitrenoids; enantioselective intra- and intermolecular couplings; and more. Part 2 looks at: C-H activation involved in stereodiscriminant step; planar chirality; diastereoselective formation of alkenes through C(sp2)?H bond activation; amongst other methods. -Covers one of the most rapidly developing fields in organic synthesis and catalysis -Clearly structured in two parts (activation of sp3- and activation of sp2-H bonds) -Edited by two leading experts in C-H activation in asymmetric synthesis CH-Activation for Asymmetric Synthesis will be of high interest to chemists in academia, as well as those in the pharmaceutical and agrochemical industry.

Greener Synthesis of Organic Compounds

Greener Synthesis of Organic Compounds

Author: Ahindra Nag

Publisher: CRC Press

Published: 2022-05-30

Total Pages: 791

ISBN-13: 1000545121

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This book provides an interdisciplinary, integrative overview of environmental problem-solving using mild reaction conditions, green reagents, waste free and energy efficient synthesis in both industry and academic world. Discussions include a broad, integrated perspective on sustainability, integrated risk, multi-scale changes and impacts taking place within ecosystems worldwide. Features: This book serves as a reference book for scientific investigators who need to do greener synthesis of organic compounds, drugs and natural products under mild reaction condition using green reagents, eco-friendly catalysts and benign reaction mediums over traditional synthetic processes which is a key driving force of scientists. Greener synthesis of multiple value-added heterocycles opens up a new horizon towards the organic catalysis and for this purpose, development of natural resources acts as an effective catalyst. Using environmentally friendly reaction medium e.g. ACC, WETSA, WEBSA have been used for the synthesis of some crucial heterocyclic scaffolds such as bisenols and 2-amino-4H-pyrans, tetraketones, pyrans, and biaryls. This book can also be used as a textbook for graduate and post graduate level courses for students. Furthermore, the problems with answers in book will add better understanding for students.


Book Synopsis Greener Synthesis of Organic Compounds by : Ahindra Nag

Download or read book Greener Synthesis of Organic Compounds written by Ahindra Nag and published by CRC Press. This book was released on 2022-05-30 with total page 791 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book provides an interdisciplinary, integrative overview of environmental problem-solving using mild reaction conditions, green reagents, waste free and energy efficient synthesis in both industry and academic world. Discussions include a broad, integrated perspective on sustainability, integrated risk, multi-scale changes and impacts taking place within ecosystems worldwide. Features: This book serves as a reference book for scientific investigators who need to do greener synthesis of organic compounds, drugs and natural products under mild reaction condition using green reagents, eco-friendly catalysts and benign reaction mediums over traditional synthetic processes which is a key driving force of scientists. Greener synthesis of multiple value-added heterocycles opens up a new horizon towards the organic catalysis and for this purpose, development of natural resources acts as an effective catalyst. Using environmentally friendly reaction medium e.g. ACC, WETSA, WEBSA have been used for the synthesis of some crucial heterocyclic scaffolds such as bisenols and 2-amino-4H-pyrans, tetraketones, pyrans, and biaryls. This book can also be used as a textbook for graduate and post graduate level courses for students. Furthermore, the problems with answers in book will add better understanding for students.

Expanding the Scope of a Diels-Alder Approach to Biaryl Synthesis

Expanding the Scope of a Diels-Alder Approach to Biaryl Synthesis

Author: Johanna Perkins Schwartz

Publisher:

Published: 2010

Total Pages: 952

ISBN-13:

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A Diels-Alder approach to biaryls (DAB) has been applied towards the synthesis of highly substituted, programmable biaryl templates. Tri- and tetra-ortho-substituted biaryls can be produced in just three to four steps from commercially available materials utilizing the Diels-Alder [4+2] cycloaddition. The methods described herein will illustrate the ability of mono and disubstituted aryl acetylenic compounds to perform effectively as dienophiles in the Diels-Alder reaction. Both acyclic and cyclic dienes have been implemented in our DAB process, with the latter requiring milder reaction conditions and exhibiting higher yields. The application of our DAB strategy towards the synthesis of biaryls has provided rapid entry to challenging substitution patterns that are not readily available by traditional coupling methods. Aryl acetylenes that possess aryl / alkyl stannyl substituents undergo the cycloaddition / cycloreversion reaction with bisoxygenated dienes to produce truly programmable biaryl templates that are readily functionalized to give access to compounds that are not readily accessible via traditional methods. Efforts to functionalize these biaryl templates led to the discovery of a novel boroxine-based Suzuki coupling strategy that can efficiently convert the sterically-encumbered chlorine-carbon bond to various aryl and alkyl groups giving rise to functionalized tetra-ortho-substituted biaryls that cannot be produced by traditional metal-mediated aryl-aryl bond formation. The syntheses of three unique tetra-ortho-substituted biaryl compounds were accomplished and these compounds were evaluated as potential ligands in aldol and hetero-Diels-Alder reactions. During the course of this work, a general method for the resolution of the biaryl compounds was illustrated that provided an efficient method for the separation of the atropisomers of our biaryl compounds. In addition, an efficient method for the construction of chiral biaryl amino acids was established. During the course of this work, the ability to construct a biaryl amino acid template was established, and the resolution of this template was accomplished using the chiral amine, brucine. Using this template, we were able to construct a small peptide containing a point-chiral amino acid at the C terminus of the biaryl template.


Book Synopsis Expanding the Scope of a Diels-Alder Approach to Biaryl Synthesis by : Johanna Perkins Schwartz

Download or read book Expanding the Scope of a Diels-Alder Approach to Biaryl Synthesis written by Johanna Perkins Schwartz and published by . This book was released on 2010 with total page 952 pages. Available in PDF, EPUB and Kindle. Book excerpt: A Diels-Alder approach to biaryls (DAB) has been applied towards the synthesis of highly substituted, programmable biaryl templates. Tri- and tetra-ortho-substituted biaryls can be produced in just three to four steps from commercially available materials utilizing the Diels-Alder [4+2] cycloaddition. The methods described herein will illustrate the ability of mono and disubstituted aryl acetylenic compounds to perform effectively as dienophiles in the Diels-Alder reaction. Both acyclic and cyclic dienes have been implemented in our DAB process, with the latter requiring milder reaction conditions and exhibiting higher yields. The application of our DAB strategy towards the synthesis of biaryls has provided rapid entry to challenging substitution patterns that are not readily available by traditional coupling methods. Aryl acetylenes that possess aryl / alkyl stannyl substituents undergo the cycloaddition / cycloreversion reaction with bisoxygenated dienes to produce truly programmable biaryl templates that are readily functionalized to give access to compounds that are not readily accessible via traditional methods. Efforts to functionalize these biaryl templates led to the discovery of a novel boroxine-based Suzuki coupling strategy that can efficiently convert the sterically-encumbered chlorine-carbon bond to various aryl and alkyl groups giving rise to functionalized tetra-ortho-substituted biaryls that cannot be produced by traditional metal-mediated aryl-aryl bond formation. The syntheses of three unique tetra-ortho-substituted biaryl compounds were accomplished and these compounds were evaluated as potential ligands in aldol and hetero-Diels-Alder reactions. During the course of this work, a general method for the resolution of the biaryl compounds was illustrated that provided an efficient method for the separation of the atropisomers of our biaryl compounds. In addition, an efficient method for the construction of chiral biaryl amino acids was established. During the course of this work, the ability to construct a biaryl amino acid template was established, and the resolution of this template was accomplished using the chiral amine, brucine. Using this template, we were able to construct a small peptide containing a point-chiral amino acid at the C terminus of the biaryl template.