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Author: David A. Petrone Publisher: Springer ISBN: 3319775073 Category : Science Languages : en Pages : 392
Book Description
This book investigates the use of palladium modified by bulky ligands as catalysts for new chemical transformations that rapidly assemble several classes of complex heterocyles. It documents the development of new chemical reactions involving carbon–carbon (C‒C) and carbon–halogen (C‒X) bond formation in the context of alkene difunctionalization and dearomatization reactions. Due to the ubiquity of heterocycles in bioactive natural products and life-improving pharmaceutical treatments, a long-term goal for synthetic organic chemists has been to develop novel and creative heterocycle syntheses that illicit a high degree of product diversity and are characterized by mild reaction conditions and limited waste production. A considerable fraction of leading pharmaceutical drugs contain at least one heterocycle within their chemical structure, and their prevalence in these technologies is strong evidence that the fundamental curiosities of organic chemistry lead to real-world solutions for the health and wellness of the global population.
Author: David A. Petrone Publisher: Springer ISBN: 3319775073 Category : Science Languages : en Pages : 392
Book Description
This book investigates the use of palladium modified by bulky ligands as catalysts for new chemical transformations that rapidly assemble several classes of complex heterocyles. It documents the development of new chemical reactions involving carbon–carbon (C‒C) and carbon–halogen (C‒X) bond formation in the context of alkene difunctionalization and dearomatization reactions. Due to the ubiquity of heterocycles in bioactive natural products and life-improving pharmaceutical treatments, a long-term goal for synthetic organic chemists has been to develop novel and creative heterocycle syntheses that illicit a high degree of product diversity and are characterized by mild reaction conditions and limited waste production. A considerable fraction of leading pharmaceutical drugs contain at least one heterocycle within their chemical structure, and their prevalence in these technologies is strong evidence that the fundamental curiosities of organic chemistry lead to real-world solutions for the health and wellness of the global population.
Author: Nur-E. Alom Publisher: ISBN: Category : Alkenes Languages : en Pages : 217
Book Description
N, S- and N, O-containing heterocycles are ubiquitous structural motifs in pharmaceuticals, agrochemicals, and bioactive natural products. These types of compounds exhibit a broad range of bioactivities such as anti-cancer, anti-HIV, antibiotics, and antidepressants. To gain access to those heterocycles, alkene sulfenoamination and alkene oxyamination have been considered as powerful strategies because of its ability to rapidly increase the molecular complexity and functional diversity. Moreover, the wide availability of alkenes in natural products and commercial sources, in addition to the ease of synthetic accesses make these alkene functionalization strategies more appealing in the synthetic community for the modular synthesis of those heterocycles. Our group is interested in the utilization of classic halonium ion as a regioselective template for the functionalization of alkenes. The research efforts presented in this dissertation focus on the development of simple and efficient methods for alkene sulfenoamination and alkene oxyamination by demonstrating a series of alkene sulfenoamination protocols for accessing interesting N, S-containing heterocycles. In Chapter 2, a simple and convenient method for the synthesis of thiazoline from readily available chemical feedstocks such as alkenes and thioamides is described. The reaction goes through the in-situ generation of 1,2-dibromoalkane from the bromination of alkene, followed by the nucleophilic attack of thioamide on the 1,2-dibromoalkane intermediate leading to thiazoline formation. The synthetic application of this method was further demonstrated by hydrolysis of thiazoline to 1,2-amino thiol and oxidation to thiazole, a common scaffold in drugs. In Chapter 3, the regio- and stereoselective sulfenoamination of alkene with thioimidazoles for the synthesis of N, S-containing heterocycle is reported. In this reaction, Selectfluor was used as a halogen source to convert the nucleophilic sulfur reagent into an electrophilic sulfur source through the formation of a sulfur-fluorine bond. Nucleophilic attack of an alkene on the sulfur electrophile led to the formation of a thiiranium ion intermediate, then intramolecular cyclization on thiiranium ion intermediate or open carbocation resulted in the product formation. The opposite regioisomer of the product could also be achieved by using bromine as a halogen source. This method exhibited good functional group tolerance and a broad range of substrate scope in a highly regio- and stereoselective manner. In Chapter 4, an efficient approach for the synthesis of 1,4-benzothiazine via alkene sulfenoamination is presented. This method is an improvement over our previous two strategies, in which we can use a catalytic amount of an iodide salt, that offers an environmentally benign and more economic strategy for alkene sulfenoamination. Moreover, the use of unprotected aminothiophenol as a coupling partner represents another significant advance in accessing 1,4-benzothiazine. The reaction proceeds through inversion of the thiol polarity with the formation of a sulfur-iodine bond. The investigation of the mechanism suggests that both polar thiiranium and radical pathways are plausible in this reaction. In Chapter 5, the development of a method for the alkylation of arene using alcohol via carbon-carbon bond formation is disclosed. The highlighting feature of this reaction is the utilization of an alkene as a catalyst for iodonium formation that can activate an alcohol, leading to the generation of the product with an all-carbon quaternary centers. The method shows a good functional group tolerance with a wide range of arene and alcohol substrate scope. This strategy can be extended to the formation of sterically congested carbon-heteroatom bonds. In addition, this method is chemoselective for tertiary alcohols in preference to the primary and secondary alcohols. In Chapter 6, an iodide-catalyzed alkene oxyamination reaction for the synthesis of oxazolidinone is discovered. The reaction utilizes unfunctionalized carbamate as a nucleophilic coupling partner, and Selectfluor as an oxidant to oxidize iodide to iodine. The reaction proceeds through the generation of catalytic iodonium intermediate, followed by nucleophilic attack of carbamate, leading to the formation of oxazolidinone product. The complementary regioisomeric product can also be achieved utilizing NBS instead as a halogen source.
Author: Jianbo Wang Publisher: Springer ISBN: 364231824X Category : Science Languages : en Pages : 283
Book Description
Stereoselective Synthesis of Tetrasubstituted Alkenes via Torquoselectivity-Controlled Olefination of Carbonyl Compounds with Ynolates, by Mitsuru Shindo and Kenji Matsumoto.- Stereoselective Synthesis of Z-Alkenes, by Woon-Yew Siau, Yao Zhang and Yu Zhao.- Stereoselective Synthesis of Mono-fluoroalkenes, by Shoji Hara.- Recent Advances in Stereoselective Synthesis of 1,3-Dienes, by Michael De Paolis, Isabelle Chataigner and Jacques Maddaluno.- Selective Olefination of Carbonyl Compounds via Metal-Catalyzed Carbene Transfer from Diazo Reagents, by Yang Hu and X. Peter Zhang.- Selective Alkene Metathesis in the Total Synthesis of Complex Natural Product, by Xiaoguang Lei and Houhua Li.- Olefination Reactions of Phosphorus-Stabilized Carbon Nucleophiles, by Yonghong Gu and Shi-Kai Tian.- Alkene Synthesis Through Transition Metal-Catalyzed Cross-Coupling of N-Tosylhydrazones, by Yan Zhang and Jianbo Wang.
Author: Peter Metz Publisher: Springer ISBN: 3540447261 Category : Science Languages : en Pages : 210
Book Description
Keeping up with the advances in modern heterocyclic chemistry is essential for many of our colleagues in academia and industry. It is the aim of this series on "Stereoselective Heterocyclic Synthesis" to assist the chemical community in this respect by presenting a selection of exciting recent developments. As it was for the first two volumes (1997), the stereoselective synthesis of - or with the aid of - heterocycles is the common motif for all the chapters in this third volume. I am very glad that again leading researchers in this area have contrib- ed highly stimulating accounts with up-to-date coverage. "Stereoselective Heterocyclic Synthesis 111" features chapters on "Stereoselective Intramolecular J,3-Dipolar Cycloadditions" by I.N.N. Nambothiiri and A. Hassner giving an in depth survey of the generation and synthetic application of valuable 1,3-dipoles, "4-Acetoxy- and 4-Cyano-12-dioxanes in Synthesis" by C.J. Sinz and S.D. Rychnovsky presenting a comprehensive summary of the utility of the versatile title compounds in natural products synthesis, "The Synthetic Potential of Three-Membered Ring Aza-Heterocycles" by B. Zwanenburg and l? ten Holte highlighting the fascinating chemistry of aziridine and azirine carboxylic esters, and '(Synthesis of Medium-Sized Ring Lactams" by U. Nubbemeyer discussing a wide range of modern strategies for the stereoselective preparation of these important heterocycles
Author: John P. Wolfe Publisher: Springer ISBN: 3642388809 Category : Science Languages : en Pages : 276
Book Description
Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Carboamination or Carboalkoxylation Reactions, by John P. Wolfe Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Diamination, Aminoalkoxylation, or Dialkoxylation Reactions, by Sherry R. Chemler Synthesis of Heterocycles via Metal-Catalyzed Wacker-Type Oxidative Cyclization Reactions of Alkoxy- or Amino-Alkenes, by Wanbin Zhang Synthesis of Saturated Heterocycles via Metal-Catalyzed Hydroamination or Hydroalkoxylation Reactions, by Lisa D. Julian Synthesis of Saturated Heterocycles via Metal-Catalyzed Allylic Alkylation Reactions, by Aaron Aponick Synthesis of Heterocycles via Metal-Catalyzed Cascade/Domino Reactions that Generate a C–N or C–O Bond, by Mark Lautens Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions that Generate a C–N or C–O Bond, by Jerome Waser
Author: Viktor V. Zhdankin Publisher: John Wiley & Sons ISBN: 1118341309 Category : Science Languages : en Pages : 630
Book Description
Hypervalent Iodine Chemistry is the first comprehensive text covering all of the main aspects of the chemistry of organic and inorganic polyvalent iodine compounds, including applications in chemical research, medicine, and industry. Providing a comprehensive overview of the preparation, properties, and synthetic applications of this important class of reagents, the text is presented in the following way: The introductory chapter provides a historical background and describes the general classification of iodine compounds, nomenclature, hypervalent bonding, structural features, and the principles of reactivity of polyvalent iodine compounds. Chapter 2 gives a detailed description of the preparative methods and structural features of all known classes of organic and inorganic derivatives of polyvalent iodine. Chapter 3, the key chapter of the book, deals with the many applications of hypervalent iodine reagents in organic synthesis. Chapter 4 describes the most recent achievements in hypervalent iodine catalysis. Chapter 5 deals with recyclable polymer-supported and nonpolymeric hypervalent iodine reagents. Chapter 6 covers the "green" reactions of hypervalent iodine reagents under solvent-free conditions or in aqueous solutions. The final chapter provides an overview of the important practical applications of polyvalent iodine compounds in medicine and industry. This book is aimed at all chemists interested in iodine compounds, including academic and industrial researchers in inorganic, organic, physical, medicinal, and biological chemistry. It will be particularly useful to synthetic organic and inorganic chemists, including graduate and advanced undergraduate students. It comprehensively covers the green chemistry aspects of hypervalent iodine chemistry, making it especially useful for industrial chemists.
Author: Erick M. Carreira Publisher: John Wiley & Sons ISBN: 9783527324521 Category : Science Languages : en Pages : 664
Book Description
Die wichtigsten und nützlichsten Methoden der modernen stereoselektiven Synthese sind in diesem Band zusammengefasst. Viele anschauliche Beispiele für die Darstellung von Wirkstoffen und Naturstoffen regen zur gezielten Abwandlung und Integration in eigene Synthesewege an. Dabei geht es den Autoren weniger darum, das Gebiet in seiner Gesamtheit darzustellen; vielmehr versuchen sie, die wirklich grundlegenden Ansätze auszuwählen, die jeder organische Synthesechemiker kennen und anwenden sollte.
Author: Alfred Hassner Publisher: Springer ISBN: 3540783717 Category : Science Languages : en Pages : 239
Book Description
Heterocyclic chemistry is the biggest branch of chemistry covering two-thirds of the chemical literature. This series covers hot topics of frontier research summarized by reputed scientists in the field.
Author: David A. Petrone
Author: David A. Petrone
Author: David Petrone
Author: David Petrone
Author: Nur-E. Alom
Author: Jianbo Wang
Author: Peter Metz
Author: John P. Wolfe
Author: Viktor V. Zhdankin
Author: Erick M. Carreira
Author: Alfred Hassner