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Author: Christian A Malapit Publisher: ISBN: Category : Electronic dissertations Languages : en Pages :
Book Description
Heterocycles are present in more than half of organic compounds. For organic chemists, they are valued as synthetic targets or scaffolds to construct valuable products. For the past two decades, the Howell group has made contributions towards the synthesis and applications of 4-membered heterocyclic compounds, such as oxetanes and beta-lactones. Most of the previously reported transformations that involve strained heterocyclic compounds rely on traditional methods in which rendering the reaction with good and predictable selectivity (regio-, chemo- and stereoselectivity) is challenging. The works described took advantage of the intrinsic reactivity of strained heterocycles and combined that with the highly selective transformations promoted by transition metal (TM) catalysts. Three successful methodologies were developed. Chapter 1 describes the discovery and scope of a novel Pt-catalyzed expansion of spirocyclopropyl oxetanes to synthetically useful 3-methylenetetrahydrofurans. This unprecedented oxetane expansion was realized via cyclopropane activation under platinum catalysis. Mechanistic studies, through 13C-labelling and 13C-DEPT NMR analyses, suggested that the oxetane expansion was promoted by a regioselective carbon-carbon bond activation of cyclopropane with platinum. Chapter 2 describes two transition metal catalyzed transformations of alpha-methylene-beta-lactones. First is a Rh-catalyzed conjugate addition with aryl boronic acids to access various beta-lactones. beta-Lactones are highly privileged synthetic products and intermediates. They have been shown to elicit serine hydrolase inhibition. They are also used as intermediates to obtain difunctionalized acyclic compounds, and this was the goal in the next method. The second method developed involves a chemoselective opening of beta-lactones to form beta-hydroxy amides. Ring opening of beta-lactones with several nucleophiles typically provide a mixture of two major products; opening via the (a) alkyl C–O bond, or (b) the acyl C–O bond. The selective ring-opening was realized via activation of acyl carbon-oxygen bond under palladium catalysis. Under the developed conditions, several beta-lactones were selectively opened with various amine nucleophiles and gave beta-hydroxy amides as sole product. This method was also translated to a Pd-catalyzed asymmetric kinetic resolution of racemic to enantioenriched beta-lactones.
Author: Christian A Malapit Publisher: ISBN: Category : Electronic dissertations Languages : en Pages :
Book Description
Heterocycles are present in more than half of organic compounds. For organic chemists, they are valued as synthetic targets or scaffolds to construct valuable products. For the past two decades, the Howell group has made contributions towards the synthesis and applications of 4-membered heterocyclic compounds, such as oxetanes and beta-lactones. Most of the previously reported transformations that involve strained heterocyclic compounds rely on traditional methods in which rendering the reaction with good and predictable selectivity (regio-, chemo- and stereoselectivity) is challenging. The works described took advantage of the intrinsic reactivity of strained heterocycles and combined that with the highly selective transformations promoted by transition metal (TM) catalysts. Three successful methodologies were developed. Chapter 1 describes the discovery and scope of a novel Pt-catalyzed expansion of spirocyclopropyl oxetanes to synthetically useful 3-methylenetetrahydrofurans. This unprecedented oxetane expansion was realized via cyclopropane activation under platinum catalysis. Mechanistic studies, through 13C-labelling and 13C-DEPT NMR analyses, suggested that the oxetane expansion was promoted by a regioselective carbon-carbon bond activation of cyclopropane with platinum. Chapter 2 describes two transition metal catalyzed transformations of alpha-methylene-beta-lactones. First is a Rh-catalyzed conjugate addition with aryl boronic acids to access various beta-lactones. beta-Lactones are highly privileged synthetic products and intermediates. They have been shown to elicit serine hydrolase inhibition. They are also used as intermediates to obtain difunctionalized acyclic compounds, and this was the goal in the next method. The second method developed involves a chemoselective opening of beta-lactones to form beta-hydroxy amides. Ring opening of beta-lactones with several nucleophiles typically provide a mixture of two major products; opening via the (a) alkyl C–O bond, or (b) the acyl C–O bond. The selective ring-opening was realized via activation of acyl carbon-oxygen bond under palladium catalysis. Under the developed conditions, several beta-lactones were selectively opened with various amine nucleophiles and gave beta-hydroxy amides as sole product. This method was also translated to a Pd-catalyzed asymmetric kinetic resolution of racemic to enantioenriched beta-lactones.
Author: András Kotschy Publisher: Springer Science & Business Media ISBN: 9781402036248 Category : Science Languages : en Pages : 224
Book Description
"Heterocycles from Transition Metal Catalysis: Formation and Functionalization" provides a concise summary of the prominent role of late transition metal (palladium, nickel, copper) catalysed processes in the synthesis and functionalization of heterocyclic systems. It gives an introduction to catalytic transformations, an overview of the most important reaction types, and presents synthetically useful catalytic processes classified by the target system and the type of transformation. The book provides a representative selection of transition metal catalysed reactions transformations that are relevant in heterocyclic chemistry. In this way, the authors present a useful resource for members of the academic community looking for a textbook as well as industrial chemists in search of a reference book. This book will be an invaluable resource for synthetic chemists, medicinal chemists, and those more generally interested in applied catalysis.
Author: Daniel Sole Publisher: Academic Press ISBN: 0128116528 Category : Science Languages : en Pages : 368
Book Description
Advances in Transition-Metal Mediated Heterocyclic Synthesis provides an overview of recent catalytic reactions involving transition metals to produce heterocyclic compounds. The book is organized according to the type of transformation used to achieve the synthesis of the heterocyclic systems (mainly aza- and oxa-heterocycles). As such, it covers recent applications on the synthesis of heterocycles, also describing the details of the novel transformations in a didactic manner to motivate readers in search of new catalytic processes. The editors have included state-of-the-art strategies, including transition-metal reactions involving unsaturated systems (reactions of allenes, new gold(I)-catalyzed reactions, and Prins reaction). Chapters highlight the versatility of organopalladium chemistry dealing with carbonylative transformations, C-H activation reactions, coupling processes, and the control of the ambiphilic character of organopalladium species. Finally, the book discusses new reactions leading to heterocycles based on C-H activation processes catalyzed by other metals (Rh, Ru, Co). Written by an outstanding team of authors who are leading experts in organometallic chemistry and organic synthesis, this book is a valuable resource not only for chemists mainly focused on synthesis, but also for those interested in reaction mechanisms involving transition metals. Helpfully organized by transformation type to stimulate the search for new synthetic processes Completely illustrated and written by global experts Includes thoughtfully selected strategies chosen by the editors to exemplify the state-of-the-art of the subject, including transition-metal reactions involving unsaturated systems, organopalladium chemistry, and metal-catalyzed C-H activation
Author: Xiao-Feng Wu Publisher: Springer ISBN: 3319249630 Category : Science Languages : en Pages : 176
Book Description
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.
Author: Xiao-Feng Wu Publisher: Elsevier ISBN: 0128040726 Category : Technology & Engineering Languages : en Pages : 117
Book Description
Transition Metal Catalyzed Furans Synthesis provides an overview of Furans, describing properties of these heterocycle compounds and covering traditional synthetic procedures for them. This book then explores catalyzed procedures for Furans synthesis in greater detail and depth then is currently available in published Reviews. Finally, this useful short work discusses natural products and bio-active compounds containing Furans, information of particular interest for their applications to medicinal and pharmaceutical chemistry. The short series Transition Metal Catalyzed Heterocycles Synthesis Series, authored by Xiao-Feng Wu, summarizes recent achievements on heterocycles synthesis with transition metal as the catalysts, with each volume dedicated to one heterocycle compound. Brief, focused review of this active research area, Furans synthesis via transition metal catalysis Useful coverage of furans properties and procedures, as well as relevant Furan-containing natural products First volume in short work series, "Transition Metal-Catalyzed Heterocycles Synthesis"
Author: Jianbo Wang Publisher: John Wiley & Sons ISBN: 3527829156 Category : Science Languages : en Pages : 450
Book Description
Presents an up-to-date overview of the rapidly growing field of carbene transformations Carbene transformations have had an enormous impact on catalysis and organometallic chemistry. With the growth of transition metal-catalyzed carbene transformations in recent decades, carbene transformations are today an important compound class in organic synthesis as well as in the pharmaceutical and agrochemical industries. Edited by leading experts in the field, Transition Metal-Catalyzed Carbene Transformations is a thorough summary of the most recent advances in the rapidly expanding research area. This authoritative volume covers different reaction types such as ring forming reactions and rearrangement reactions, details their conditions and properties, and provides readers with accurate information on a wide range of carbene reactions. Twelve in-depth chapters address topics including carbene C-H bond insertion in alkane functionalization, the application of engineered enzymes in asymmetric carbene transfer, progress in transition-metal-catalyzed cross-coupling using carbene precursors, and more. Throughout the text, the authors highlight novel catalytic systems, transformations, and applications of transition-metal-catalyzed carbene transfer. Highlights the dynamic nature of the field of transition-metal-catalyzed carbene transformations Summarizes the catalytic radical approach for selective carbene cyclopropanation, high enantioselectivity in X-H insertions, and bio-inspired carbene transformations Introduces chiral N,N'-dioxide and chiral guanidine-based catalysts and different transformations with gold catalysis Discusses approaches in cycloaddition reactions with metal carbenes and polymerization with carbene transformations Outlines multicomponent reactions through gem-difunctionalization and transition-metal-catalyzed cross-coupling using carbene precursors Transition Metal-Catalyzed Carbene Transformations is essential reading for all chemists involved in organometallics, including organic and inorganic chemists, catalytic chemists, and chemists working in industry.
Author: Jianbo Wang Publisher: John Wiley & Sons ISBN: 3527347992 Category : Science Languages : en Pages : 450
Book Description
Presents an up-to-date overview of the rapidly growing field of carbene transformations Carbene transformations have had an enormous impact on catalysis and organometallic chemistry. With the growth of transition metal-catalyzed carbene transformations in recent decades, carbene transformations are today an important compound class in organic synthesis as well as in the pharmaceutical and agrochemical industries. Edited by leading experts in the field, Transition Metal-Catalyzed Carbene Transformations is a thorough summary of the most recent advances in the rapidly expanding research area. This authoritative volume covers different reaction types such as ring forming reactions and rearrangement reactions, details their conditions and properties, and provides readers with accurate information on a wide range of carbene reactions. Twelve in-depth chapters address topics including carbene C-H bond insertion in alkane functionalization, the application of engineered enzymes in asymmetric carbene transfer, progress in transition-metal-catalyzed cross-coupling using carbene precursors, and more. Throughout the text, the authors highlight novel catalytic systems, transformations, and applications of transition-metal-catalyzed carbene transfer. Highlights the dynamic nature of the field of transition-metal-catalyzed carbene transformations Summarizes the catalytic radical approach for selective carbene cyclopropanation, high enantioselectivity in X-H insertions, and bio-inspired carbene transformations Introduces chiral N,N'-dioxide and chiral guanidine-based catalysts and different transformations with gold catalysis Discusses approaches in cycloaddition reactions with metal carbenes and polymerization with carbene transformations Outlines multicomponent reactions through gem-difunctionalization and transition-metal-catalyzed cross-coupling using carbene precursors Transition Metal-Catalyzed Carbene Transformations is essential reading for all chemists involved in organometallics, including organic and inorganic chemists, catalytic chemists, and chemists working in industry.
Author: Xiao-Feng Wu Publisher: Elsevier ISBN: 0128093692 Category : Technology & Engineering Languages : en Pages : 103
Book Description
Transition Metal-Catalyzed Pyrimidine Synthesis: Transition Metal-Catalyzed Heterocycle Synthesis Series provides an overview of pyrimidine, describing properties of these heterocycle compounds and the traditional synthetic procedures used for them. The book then explores catalyzed procedures for pyrimidine synthesis in greater detail and depth than is currently available in published review articles. This volume is part of the short series authored by Xiao-Feng Wu that summarizes recent achievements on heterocycle synthesis with transition metals as catalysts, with each volume dedicated to one heterocycle compound. Offers a brief, focused review of the active research in pyrimidine synthesis via transition metal catalysis Provides useful coverage of pyrimidine properties and both intermolecular and intramolecular cyclization Volume Three in Elsevier’s short work series, Transition Metal-Catalyzed Heterocycles Synthesis Provides greater detail and depth than is currently available in published review articles
Author: Christian A Malapit
Author: Christian A Malapit
Author: András Kotschy
Author: Daniel Sole
Author: Xiao-Feng Wu
Author: Xiao-Feng Wu
Author: Malcolm P. Huestis
Author: Xiao-Feng Wu
Author: Jianbo Wang
Author: Jianbo Wang
Author: Xiao-Feng Wu