Design and Synthesis of Sugar and Amino Acid-based Chiral Ligands and Their Use in Asymmetric Catalysis PDF Download
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Author: Cheng-Wei Tom Chang
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Author: Cheng-Wei Tom Chang
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Author: Montserrat Diéguez
Publisher: CRC Press
ISBN: 1000379000
Category : Science
Languages : en
Pages : 298
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Book Description
Many new drugs on the market are chiral compounds, that is, they can exist in two non-superimposable mirror-image forms. Asymmetric catalysis encompasses a large variety of processes for obtaining such compounds. The performance of the catalyst in those processes largely depends on the ligand that makes up the catalyst. This book describes the most relevant ligand libraries for some key processes, including an overview of the state of art and the key mechanistic aspects that favor a high catalytic performance. Key Features: The book presents historical content from the time of discovery for each family of ligands. Provides a description of the synthetic route and the ligand library's application in various catalytic asymmetric reactions Suitable as supplementary reading for courses targeting the design, synthesis and application of chiral catalysts, asymmetric catalysis and sustainable production Edited by a distinguished scientist in the field, the book has a diverse audience including research groups in homogeneous catalysis, particularly asymmetric transformations
Author: Hélène Pellissier
Publisher: Royal Society of Chemistry
ISBN: 1847559247
Category : Science
Languages : en
Pages : 403
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Book Description
The goal of this book is to show the high potential of chiral sulfur-containing ligands to promote numerous asymmetric catalytic transformations. These ligands can now be recognised as real competitors to the more usual phosphorus- or nitrogen-containing ligands.
Author: Wei Li
Publisher:
ISBN:
Category :
Languages : en
Pages : 233
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Author: Qi-Lin Zhou
Publisher: John Wiley & Sons
ISBN: 3527635211
Category : Technology & Engineering
Languages : en
Pages : 670
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Book Description
Catalytic asymmetric synthesis has been one of the most active research areas in chemistry (Nobel Prize in 2001). The development of efficient chiral catalysts plays a crucial role in asymmetric catalysis. Although many chiral ligands/catalysts have been developed in the past decades, the most efficient catalysts are derived from a few core structures, called "privileged chiral catalysts". This ultimate "must have" and long awaited reference for every chemist working in the field of asymmetric catalysis starts with the core structure of the catalysts, explaining why a certain ligand or catalyst is so successful. It describes in detail the history, the basic structural characteristics, and the applications of these "privileged catalysts". This novel presentation provides readers with a much deeper insight into the topic and makes it a must-have for organic chemists, catalytic chemists, chemists working with/on organometallics, chemists in industry, and libraries. From the contents: * BINAP * Bisphosphacycles - From DuPhos and BPE to a Diverse Set of Broadly Applied Ligands * Josiphos Ligands: From Discovery to Technical Applications * Chiral Spiro Ligands * Chiral Bisoxazoline Ligands * PHOX Ligands * Chiral Salen Complexes * BINOL * TADDOLate Ligands * Cinchona Alkaloids * Proline Derivatives
Author:
Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 1006
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Author: Marc Lemaire
Publisher: Springer
ISBN: 9783642065385
Category : Science
Languages : en
Pages : 0
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Book Description
The use of phosphine derivatives has historically induced the tremendous development of catalysis (both non-asymmetric and asymmetric). Although the chemistry of amines is more documented, the use of nitrogen-containing ligands only appeared recently. Nevertheless, during the last ten years, the results describing chiral diamine preparations and their uses in asymmetric catalysis and synthesis are increasing faster than their phosphorus counterparts. The reader will find in this volume the most recent methods for the synthesis of chiral diamines as well as their applications in asymmetric catalysis of CC bond formation. Particular attention will be given to spartein and derivatives of such diamines. Recently, the particular properties and the chemistry of amines allowed to obtain catalysts easy to separate and recycle and new types of ligands such as diaminocarbenes, ureas and thioureas. Finally, the complexing properties of some diamines allowed the formation of complexes with chirality "at the metal " which is of major theoretical interest and presents numerous potential applications.
Author: Jacek Wojaczynski
Publisher: John Wiley & Sons
ISBN: 3527834192
Category : Science
Languages : en
Pages : 692
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Book Description
Chiral Building Blocks in Asymmetric Synthesis A comprehensive introduction to the important classes of chiral building blocks Chirality — the asymmetric quality found in certain chemical compounds — plays an essential role in our world: chiral compounds can be found in biology, pharmaceutical compounds, agrochemicals, and fragrances. The stereoselective preparation of these complex molecular constructions constitutes a challenge. To this end, modern asymmetric synthesis utilizes a variety of valuable and efficient reagents employed as chiral auxiliaries, metal complexes and organocatalysts in stereoselective catalysis, and enantiopure reactants termed as chiral building blocks. In Chiral Building Blocks in Asymmetric Synthesis, the achievements in the fields of preparation of and applications of chiral blocks are presented. In doing so, the book comprehensively discusses the important classes of these reactants as the key for the asymmetric synthesis of chiral molecules. As such, it is an indispensable resource about synthetic methods, as well as possible modifications and transformations of important classes of chiral compounds. It also highlights the importance of their use as reactants and auxiliaries in the preparation of more sophisticated molecules or supramolecular systems. In Chiral Building Blocks in Asymmetric Synthesis readers will also find: Organization according to the most important compound classes — e.g. amino acids, BINOL and its derivatives, terpenes, and others — with an emphasis on synthesis and application A focus on the use of chiral building blocks for the preparation of bioactive compounds and supramolecular assemblies Chiral Building Blocks in Asymmetric Synthesis is a useful reference for organic chemists, catalytic chemists, chemists in industry, medicinal chemists, pharmaceutical chemists, and the libraries that support them.
Author: Michael P. A. Lyle
Publisher:
ISBN:
Category : Asymmetric synthesis
Languages : en
Pages : 0
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Book Description
The work described in this thesis concerns the design, synthesis and evaluation of new chiral nonracemic ligands and catalysts for use in asymmetric reactions. A series of chiral nonracemic chloroacetals were prepared from 2-chloro-4- methyl-6,7-dihydro-5H-[l]pyrindine-7-one and a variety of C2-symmetric and chiral nonracemic 1,2-ethanediols (R = Me, i-Pr and Ph). These chloroacetals were further elaborated, in a modular fashion, to provide a series of chiral ligands and catalysts. A new class of C2-symmetric 2,2'-bipyridyl ligands were prepared in one step fiom the chloroacetals via a nickel(0)-mediated homo-coupling reaction. These ligands were then evaluated as chiral directors in copper@)-catalyzed asymmetric cyclopropanation reactions of styrene and diazoesters (up to 44% ee). A chiral pyridine N-oxide and a C2-symmetric 2,2'-bipyridyl N, N'-dioxide were also prepared by direct oxidation of the corresponding pyridine and the 2,2'-bipyridine, respectively. These chiral N-oxides were evaluated as chiral catalysts in desymmeterization reactions of cis-stilbene oxide (up to 20% ee). A series of pyridylphosphine ligands (P, N-ligands) were subsequently prepared in two steps from the chloroacetals via a Suzuki coupling reaction with orthofluorophenylboronic and on subsequent displacement of the fluoride with the potassium anion of diphenylphosphine. These ligands were then evaluated in palladium-catalyzed asymmetric allylic substitution reactions of racemic 3-acetoxy-l,3-diphenyl-1-propene with dimethyl malonate. Optimization of the reaction conditions resulted in the formation of the alkylated product in excellent yield (91%) and in high enantiomeric excess (90%). A related chiral nonracemic and C2-symmetric 2,2'-bipyridyl ligand was prepared from 2-chloro-4-methyl-5H-[llpyrindine. This pyrindine was prepared from a common intermediate that was used in the synthesis of the first generation of ligands. The chirality of this second generation ligand was installed by a Sharpless asymmetric dihydroxylation reaction (90% ee). The subsequently elaborated 2,2'-bipyridyl ligand (enriched to>99% ee) was then evaluated in copper(1)-catalyzed asymmetric cyclopropanation reactions of alkenes and diazoesters. In the case of the reaction of para-fluorostyrene and tert-butyl diazoacetate, the corresponding cyclopropane was formed in good diastereoselectivity (92:8) and in excellent enantioselectivity (99% ee). This ligand was also evaluated in copper(I1)-catalyzed asymmetric Friedel-Crafts alkylation reactions of various substituted indoles (up to 90% ee) and in copper(1)- catalyzed asymmetric allylic oxidation reactions of cyclic alkenes with tert-butyl peroxybenzoate (up to 9 1 % ee).
Author: Iwao Ojima
Publisher: John Wiley & Sons
ISBN: 047122054X
Category : Science
Languages : en
Pages : 879
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Book Description
From the reviews of the First Edition . . . "An excellent text . . . will no doubt provide the benchmark for comparative works for many years."-Journal of the American Chemical Society "A resounding success . . . the definitive current summaries on their respective subjects."-Synthesis Since this important work was first published in 1993, the field of catalytic asymmetric synthesis has grown explosively, spawning effective new methods for obtaining enantiomerically pure compounds on a large scale and stimulating new applications in diverse fields-from medicine to materials science. Catalytic Asymmetric Synthesis, Second Edition addresses these rapid changes through new or substantially revised contributions from highly recognized world leaders in the field. It presents detailed accounts of the most important catalytic asymmetric reactions known today, discusses recent advances, and retains from the previous edition essential and intriguing information on the initial development of certain processes. An excellent working resource for academic researchers and industrial chemists alike, the Second Edition features: * Contributions from Noyori, Sharpless, Kagan, Trost, Overman, Shibasaki, Doyle, Okamoto, Bolm, Carreira, and many other internationally renowned authorities * New chapters on asymmetric carbometallations, asymmetric amplification and autocatalysis, and asymmetric polymerization * Extended coverage of asymmetric carbene reactions, including asymmetric intramolecular carbene insertion to C-H bonds as well as asymmetric dihydroxylation and aminohydroxylation * Extended coverage of asymmetric carbon-carbon bond-forming reactions and applications * An appendix listing all chiral ligands in the book
