Comprehensive Chirality, 1st Edition,Hisashi Yamamoto,Erick Carreira,ISBN9780080951676
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Comprehensive Chirality, 1st Edition

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Editor in Chief : Yamamoto &   Carreira  

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Imprint: Elsevier Science

ISBN: 9780080951676

Pages: 5648

A complete overview of the chiral field including research relevant to synthesis, analytic chemistry, catalysis and pharmaceuticals

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Key Features

  • Chirality research today is a central theme in chemistry and biology and is growing in importance across a number of disciplinary boundaries. These studies do not always share a unique identifying factor or subject themselves to clear and concise definitions. This work unites the different areas of research and allows anyone working or researching in chiral chemistry to navigate through the most essential concepts with ease, saving them time and vastly improving their understanding.
  •  The field of chirality counts several journals that are directly and indirectly concerned with the field. There is no reference work that encompasses the entire field and unites the different areas of research through deep foundational reviews. Comprehensive Chirality fills this vacuum, and can be considered the definitive work. It will help users apply context to the diverse journal literature offering and aid them in identifying areas for further research and/or for solving problems.
  • Chief Editors, Hisashi Yamamoto (University of Chicago) and Erick Carreira (ETH Zürich) have assembled an impressive, world-class team of Volume Editors and Contributing Authors. Each chapter has been painstakingly reviewed and checked for consistent high quality. The result is an authoritative overview which ties the literature together and provides the user with a reliable background information and citation resource.

Description

Although many books exist on the subject of chiral chemistry, they only briefly cover chiral synthesis and analysis as a minor part of a larger work, to date there are none that pull together the background information and latest advances in one comprehensive reference work. Comprehensive Chirality provides a complete overview of the field, and includes chiral research relevant to synthesis, analytic chemistry, catalysis, and pharmaceuticals. The individual chapters in each of the 9 volumes provide an in depth review and collection of references on definition, technology, applications and a guide/links to the related literature. Whether in an Academic or Corporate setting, these chapters will form an invaluable resource for advanced students/researchers new to an area and those who need further background or answers to a particular problem, particularly in the development of drugs.

Readership

Graduate students and researchers working in organic, medicinal, and biological chemistry, as well as pharmacologists and toxicologists.

Hisashi Yamamoto

Chemists' ability to perform syntheses on a routine basis is due in large part to the development of new methods for synthesizing organic molecules which would have been impossible just a few decades ago. The availability of such new methods of synthesis has increased not only the range of structures which can be assembled but also the ease and economy of synthesis. During the past 30 years of his research, Professor Hisashi Yamamoto has had a tremendous impact on the field of organic chemistry through his reports of dramatic new advances in organic synthesis. Yamamoto's publications are numerous (over 450), and almost every one of them has provided an innovative new development or idea. Applications of this original and versatile chemistry have allowed him and other scientists to realize truly efficient syntheses of organic molecules of both theoretical and practical importance.

Hisashi Yamamoto has uncovered novel aspects of Lewis and Brønsted acid catalysts in selective organic synthesis. During his career he has discovered a wide variety of powerful new synthetic reactions, reagents, and catalysts based on acid catalysis chemistry. Through his dedicated efforts, Lewis and Brønsted acid are now recognized as major tools in the synthesis of both simple and complex organic molecules. Among Yamamoto's many superb contributions the following are especially worthy of mention.

His research in the area of organoaluminum chemistry has had a great impact on synthetic organic chemistry. The strong Lewis acidity of organoaluminum compounds appears to account for their strong tendency to form a stable 1:1 complex. Thus, the coordination of molecules invariably causes a change of reactivity, and the coordinated group may be activated or deactivated depending upon the type of reaction. Furthermore, with coordination of organic molecules an auxiliary bond can become coupled to the reagent and promote the desired reaction. In short, the reagents make a combined Lewis acid - Lewis base attack on a substrate with less activation energy, a field opened by Yamamoto's early and highly original studies. His aluminum amide reagents for epoxide rearrangement, biogenetic-type terpene synthesis, and the Beckmann rearrangement-alkylation reaction sequence are notable examples.

He was intrigued by the chemistry of the carbonyl compound-Lewis acid complex and introduced the unusually bulky organoaluminum reagents, methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) and aluminum tris(2,6-diphenylphenoxide) (ATPH). These reagents were successfully utilized for the selective alkylation of cyclic ketones and aldehydes to generate equatorial alcohol and an anti-Cram type product, respectively, for trans- and cis-selective Claisen rearrangement, for regioselective Diels-Alder reaction, and for epoxide-aldehyde rearrangement. The ATPH - aromatic carbonyl complex reacts with nucleophiles selectively at the para-position of the aromatic ring to generate cyclohexadiene derivatives.

After these pioneering researches in Lewis acid chemistry, Yamamoto has become aware of the vast importance of chiral Lewis acids in modern asymmetric synthesis. In 1985, he first introduced binaphthol as a key ligand for chiral Lewis acid catalysts. This work was the forerunner of a vast quantity of present-day research on the binaththol based chiral Lewis acid catalyst. Based on his knowledge of organoaluminum chemistry, he designed a new and powerful organoaluminum catalyst for asymmetric hetero-Diels-Alder reaction. It was his Brønsted acid-Lewis acid combined system, however, which gave him a unique opportunity for the most efficient asymmetric Lewis acid catalyst for Diels-Alder reaction. A similar concept was employed for his catalytic asymmetric protonation under acidic conditions, which now creates a long sought proton induce

Affiliations and Expertise

The University of Chicago, Illinois, USA, Chubu University, Aichi, Japan

Erick Carreira

Erick M. Carreira was born in Havana, Cuba in 1963. He obtained a B.S. degree in 1984 from the University of Illinois at Urbana­Champaign under the supervision of Scott E. Denmark and a Ph.D. degree in 1990 from Harvard University under the supervision of David A. Evans. After carrying out postdoctoral work with Peter Dervan at the California Institute of Technology through late 1992, he joined the faculty at the same institution as an assistant professor of chemistry and subsequently was promoted to the rank of associate professor of chemistry in the Spring of 1996, and full professor in Spring 1997. Since September 1998, he has been full professor of Organic Chemistry at the ETH Zürich. He is the recipient of the American Chemical Society Award in Pure Chemistry, Nobel Laureate Signature Award, Fresenius Award, a David and Lucile Packard Foundation Fellowship in Science, Alfred P. Sloan Fellowship, Camille and Henry Dreyfus Teacher Scholar Award, Merck Young Investigator Award, Eli Lilly Young Investigator Award, Pfizer Research Award, National Science Foundation CAREER Award, Arnold and Mabel Beckman Young Investigator Award, and a Camille and Henry Dreyfus New Faculty Award. He is also the recipient of the Associated Students of the California Institute of Technology Annual Award in Teaching and a Richard M. Badger Award in Teaching.

His research program focuses on the asymmetric synthesis of biologically active, stereochemically complex, natural products. Target molecules are selected which pose unique challenges in asymmetric bond construction. A complex multistep synthesis endeavor provides a goal-oriented setting within which to engage in reaction innovation and design. Drawing from the areas of organometallic chemistry, coordination chemistry, and molecular recognition, Carreira's group is developing catalytic and stoichiometric reagents for asymmetric stereocontrol.

Affiliations and Expertise

ETH Zürich, Switzerland

Comprehensive Chirality, 1st Edition

Volume 1: Biological significance - Pharmacology, Pharmaceutical, Agrochemical

Introduction: Importance of chirality in biological active compounds

Cases Where Chirality May or May Not be Critical in Drug Discovery and Development: Adventures with Protease Inhibitors

The new Phosphine Ligands in asymmetric synthesis

Chiral libraries for drug discovery, an overview

Issues of chirality in the synthesis of medicinally relevant peptides

Fluorine in Medicinal Chemistry

Antituberculosis

Synthesis of chiral antibacterial agents

Anti-infectious compounds

Agrochemical products

Synthesis and biological activity of citalopram/escitalopram

Diastereo- and enantioselective syntheses of dioxolane and tetrahydrofurane

Volume 2: Synthetic Methods I - Chiral Pool and Diastereoselective Methods

Introductory Remarks

Chiral pool syntheses | Chiral pool syntheses starting from amino acids

Chiral pool syntheses | Chiral pool syntheses starting from terpenes

Chiral pool syntheses | Chiral pool syntheses starting from carbohydrates

Chiral pool syntheses | Chiral pool syntheses from arene cis-1,2-diols

Chiral pool syntheses | Chiral pool synthesis from hydroxy acids: lactic acid, tartaric acid, malic acid, 2-methyl-3-hydroxypropionic acid

Chiral pool syntheses | Chiral pool synthesis from hydroxy acids: quinic acid

General Principles of Diastereoselective Reactions | Application of rigid templates and substrate directable reactions

General Principles of Diastereoselective Reactions | Acyclic conformational control of diastereoselectivity

General Principles of Diastereoselective Reactions | Domino reactions

Selected Diastereoselective reactions | carbanion additions to ketones and aldehydes

Selected Diastereoselective reactions | Aldoltype additions

Selected Diastereoselective reactions | Enolate alkylation

Selected Diastereoselective reactions | Intramolecular Diels-Alder reactions

Selected Diastereoselective reactions | Ionic and Zwitterionic Cyclisations

Selected Diastereoselective reactions | Electrocyclizations

Selected Diastereoselective reactions | Sigmatropic rearrangements

Selected Diastereoselective reactions | C-H- Insertions

Selected Diastereoselective reactions | Free radical additions and cyclizations

Selected Diastereoselective reactions | Carbenium ion olefin cyclizations

Selected Diastereoselective reactions | Heck type cyclizations

Selected Diastereoselective reactions | Gold catalyzed cyclizations

Volume 3: Synthetic Methods II - Chiral Auxiliaries

Amino Acid Derived Auxiliaries | Simple Amino Acids and Derivatives

Amino Acid Derived Chiral Auxiliaries | Use of Oxazolidinones, Thiooxazolidinones, Imidazolones, and Thiazolidinethiones

Terpene Derived Auxiliaries | Camphor and Pinene Class Auxiliaries

Terpene Derived Auxiliaries | Menthol and Pulegone Derived Auxiliaries

Terpene Derived Auxiliaries | Miscellaneous Terpene Derived Auxiliaries

Acetogenin (polypriopionate) Derived Auxiliaries | Tartaric Acid

Acetogenin (polypriopionate) Derived Auxiliaries | Hydroxy Acids and Derivatives

Acetogenin (polypriopionate) Derived Auxiliaries | Miscellaneous Acetogenin Derived Auxiliaries

Alkaloid Derived Auxiliaries | Cinchona Alkaloids and Derivatives

Alkaloid Derived Auxiliaries | Ephedra Alkaloids

Alkaloid Derived Auxiliaries | Miscellaneous Alkaloid Derived Auxiliaries

Carbohydrate Derived Auxiliaries | Mono (and Disaccharide) Derivatives

Carbohydrate Derived Auxiliaries | Aminosaccharide and other Carbohydrate Derivitives

Synthetically Derived Auxiliaries | Ketones and Ketals

Non-Chiral Pool Derived Synthetic Auxiliaries: Use of Alcohols (including Diols) and Phenols (including BINOL)

Synthetically Derived Auxiliaries | Amines (incl Diamines), Hydrazines, and Amino Alcohols

Synthetically Derived Auxiliaries | Phosphorus Derivatives

Synthetically Derived Auxiliaries | Sulfur Derivatives (incl Sulfilamines,Ssulfoximines)

Synthetically Derived Auxiliaries | Organometallic Derivatives (Main Group

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Lithium

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Magnesium and Calcium

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Boron and Aluminum

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Silicon

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Tin and Stannanes

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Zinc

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Chromium

Stoichiometric Auxiliary Ligands For Metals and Main Group Elements | Ligands for Titanium and Zirconium

Volume 4: Synthetic Methods III - Catalytic Methods: C-C Bond Formation

Introduction

C-C bond formation (cross-coupling, Heck)

C-C bond formation (metathesis)

C-C bond formation (p-allylmetal)

C-C bond formation (reductive aldol)

C-C bond formation (transition metal-catalyzed Michael)

C-C bond formation (metal-carbene catalyzed)

C-C bond formation (enol silyl ether, Lewis acid)

C-C bond formation (enol silyl ether, Lewis base)

C-C bond formation (enol silyl ether, transmetallation)

Direct C-C bond formation (Henry, Aza-Henry)

Direct C-C bond formation ((Michael, Aldol, Mannich)

Reactions using thioamide and allylic cyanide

C-C bond formation (radical)

Cyanation of carbonyls and imines

C-C bond formation (1,2-alkylation)

C-C bond formation (1,2-alkenylation)

C-C bond formation (1,2-alkynylation)

C-C bond formation (1,2-arylation)

C-C bond formation (1,2-allylation)

Ene Reaction, Cycloaddition, and Pauson-Khand Reaction

Other C-C bond formations including Au

Volume 5: Synthetic Methods IV - Asymmetric Oxidation Reduction, C-N

Oxidation | C-O bond formation by oxidation: C-H bond activation

Oxidation | Bayer-Villager oxidation

Oxidation | Allylic

Oxidation | Epoxidation (Allylic alcohol oxidation, Homoallylic alcohol Simple C=C, Electron deficient C=C)

Oxidation | Dihydroxylation

Oxidation | Alpha-hydroxylation of carbonyls

Oxidation | C-N bond formation by oxidation: C-H bond activation

Oxidation | C-N bond formation by oxidation: C-N bond formation by oxidation (aziridines)

Oxidation | C-N bond formation by oxidation: Dinitrogen addition to double bond (diamino)

Oxidation | S-O bond formation by oxidation: S-O bond formation by oxidation

Oxidation | C-X bond formation: C-X bond formation (X = halogen, S, Se, etc.)

Reduction - hydrogenation | C=C; chemoselective

Reduction - hydrogenation | C=O; chemoselective

Reduction - hydrogenation | C=N (oximes, hydrazones)

Reduction | Hydrosilylation

Reduction | Hydroformylation C-H and C-C

Reduction | Hydrocyanation of C=C

Reduction | Hydrovinylation of C=C

Reduction | Pinacol coupling

Addition reaction | Kinetic resolution (e.g. to oxidise 50% epoxide to alcohol with water)

Addition reaction | 1,4 addition heteroatom (mercaptan, azo (DEAD) etc)

Addition reaction | Cycloaddition involving oxidation (N=N, N=O; no C-C bond formed)

Desymmetrization | meso diol (to optically active alcohol)

Desymmetrization | meso epoxide

Desymmetrization | meso anhydride

Volume 6: Synthetic Methods V - Organocatalysis

C-C bond formation | Alkylation

C-C bond formation | Michael addition

C-C bond formation | Mannich reaction

C-C bond formation | Aldol reaction with proline deriv.

C-C bond formation | Aldol reaction with non-proline deriv.

C-C bond formation | Henry

C-C bond formation | Cyanation

C-C bond formation | Allylation

C-C bond formation | (aza) Baylis-Hillman reaction

C-C bond formation | Diels-Alder reaction

C-C bond formation | Cyclopropane formation

C-C bond formation | Benzoin reaction

C-C bond formation | Friedel-Crafts

C-C bond formation | Cascade or domino reaction

C-N bond formation | a-Amination with DEAD

C-N bond formation | Aziridine formation

C-O bond formation | a-Oxygenation

C-O bond formation | Acylation of meso-diols

C-O bond formation | Kinetic resolution of sec-alcohols

C-O bond formation | Desymmetrization of acid anhydride

C-O bond formation | Epoxide formation

C-X bond formation | a-Halogenation of carbonyl compounds

C-X bond formation | Halogenation of meso-epoxides

C-X bond formation | a-Sulfenylayion, a-selenenylation

Oxidation | Epoxidation of alkenes

Oxidation | Epoxidation of enones

Reduction | Hantzsch ester reduction

Volume 7: Synthetic Methods VI - Enzymatic and Semi-Enzymatic

Introduction | General concepts

Introduction | Screening methods for enzymes

Introduction | Directed evolution of enzymes

Introduction | Cofactor recycling

Introduction | Reaction engineering

Hydrolysis & Reverse Hydrolyis | Hydrolysis/formation of esters

Hydrolysis & Reverse Hydrolyis | Hydrolysis/formation of amides

Hydrolysis and Reverse Hydrolyis | Hydrolysis of nitriles

Hydrolysis and Reverse Hydrolyis | Hydrolysis of epoxides

Hydrolysis and Reverse Hydrolyis | Halohydrin dehalogenases

Hydrolysis and Reverse Hydrolyis | Dynamic kinetic resolution

Reduction | Reduction of ketones

Reduction | Reduction of Carbon Carbon Double Bonds

Reduction | Reduction of other functional groups (e.g. nitro, azo etc.)

Oxidation | Oxidases

Oxidation | P450 Oxidations

Oxidation | Bayer-Villiger

Oxidation | Asymmetric sulfoxidations

Oxidation | Haloperoxidases

C-X Bond formation | Aldolases (C-C)

C-X Bond formation | Hydroxynitrile lyases (C-C)

C-X Bond formation | Miscellaneous C-C forming enzymes (e.g. transketolase, benzaldehyde lyase)

C-X Bond formation | Transaminases (C-N)

C-X Bond formation | Decarboxylases

Special Topics | Multi-enzyme reactions

Synthesis of carbohydrates

Industrial applications

Enzyme promiscuity

Emerging reactions

Enzymes on solid-phase

Whole-cell biotransformations

Hybrid enzymes

Polypeptide catalysis

De novo enzymes

Unnatural amino acid enzymes

Combinatorial biosynthesis

Volume 8: Separations and Analysis

Perspective and Concepts | Pasteur, Lord Kelvin

Perspective and Concepts | Notation, Enantiomeric Purity, Enantiomeric Excess and Racemic Mixtures

Perspective and Concepts | Enantiomers, Racemates and Diasteromeric Interactions

Perspective and Concepts | Biomolecular Significance

Perspective and Concepts | Pharmacological Significance

Perspective and Concepts | Chemical and Physical Significance

Perspective and Concepts | Overview of Techniques for Separating Enantiomers

Perspective and Concepts | Overview of Techniques for Assigning Stereochemistry

Perspective and Concepts | Overview of Techniques for Studying Chiral Phenomena

Perspective and Concepts | Regulatory Implications and Methodology

Physical Separations | Overview

Physical Separations | Physical Properties, Solubility, Thermodynamics

Physical Separations | Solid-state Forms and Habits

Physical Separations | Enantiomeric vs Racemic Crystallisation, Conglomerates, Deracemisation

Physical Separations | Crystallisation Control by Trace Chiral Modifiers, Seeding and Entrainment

Physical Separations | Chiral Discrimination of Enantiomers by Diastereomeric Complexation with Chiral Host Compounds

Physical Separations | Preferential Reactivity

Physical Separations | Enantiomer Enrichment

Chromatographic Separations and Analysis | Overview

Chromatographic Separations and Analysis | Synthetic Chiral Stationary Phases (Pirkle)

Chromatographic Separations and Analysis | Chiral Ion and Ligand Exchange Stationary Phases

Chromatographic Separations and Analysis | Protein and Glycoprotein Stationary Phases

Chromatographic Separations and Analysis | Cyclodextrins as Stationary Phases and Modifiers

Chromatographic Separations and Analysis | Celluloses and Polysaccharides as Stationary Phases

Chromatographic Separations and Analysis | Macrocyclic Glycopeptide Stationary Phases

Chromatographic Separations and Analysis | Ionic Liquid Stationary Phases

Chromatographic Separations and Analysis | Crown Ether Stationary Phases

Chromatographic Separations and Analysis | New Stationary Phases

Chromatographic Separations and Analysis | Chiral Mobile Phase Modifiers

Chromatographic Separations and Analysis | Diasteromeric Derivitisation for Chromatography

Chromatographic Separations and Analysis | HPLC and UPLC

Chromatographic Separations and Analysis | LC

Chromatographic Separations and Analysis | TLC

Chromatographic Separations and Analysis | GC

Chiral capillary electrophoresis (CE) and electrochromatography (CEC)

Chromatographic Separations and Analysis | SFC

Chromatographic Separations and Analysis | Chiral Detectors for Chromatography

Spectroscopic Analysis | Overview, Background, Polarised Light and Optics

Spectroscopic Analysis | Electronic Circular Dichroism

Spectroscopic Analysis | Vibrational Circular Dichroism

Spectroscopic Analysis | Synchrotron Circular Dichroism

Spectroscopic Analysis | Raman Optical Activity

Spectroscopic Analysis | Polarimetry and Optical Rotatory Dispersion

Spectroscopic Analysis | NMR and Shift Reagents

Spectroscopic Analysis | Diasteromeric Derivitisation for Spectroscopy

Spectroscopic Analysis | Exciton Coupling for Chiral Detection

Spectroscopic Analysis | Fluorescence and Chiral Reporter Molecules

Spectroscopic Analysis | Ab initio Calculation of Chiroptical Spectra

Spectroscopic Analysis | Chiral Process Analytical Technology

Spectroscopic Analysis | Chiroptical Sensors

Physical and Spectrometric Analysis | Overview

Physical and Spectrometric Analysis | Anomalous Single Crystal X-ray Diffraction

Physical and Spectrometric Analysis | Flack Enantiopole Parameter and Assignment Certainty

Physical and Spectrometric Analysis | Anomalous Powder X-ray Diffraction

Physical and Spectrometric Analysis | Synthetic Receptors

Physical and Spectrometric Analysis | Electrochemical

Physical and Spectrometric Analysis | Mass Spectrometry and Chiral Reporter Molecules

Physical and Spectrometric Analysis | Nano-detection

Biophysical Analysis | Overview

Biophysical Analysis | Detection and Analysis via Enzyme Catalysed Reactions

Biophysical Analysis | Detection and Analysis via Biomolecular Binding

Biophysical Analysis | Detection and Analysis via Biological Response - Taste and Smell

Volume 9: Industrial Applications of Asymmetric Synthesis

Introduction | Introduction to Industrial Applications

Asymmetry in the Plant | Concepts and Principles for the Scale-Up of Asymmetric Organic Reactions

Industrial Applications of Asymmetric Synthesis | Asymmetric Synthesis as an Enabler of Green Chemistry

Industrial Applications of Asymmetric Reduction of C=C Bonds

9.5 Reduction of C=O, C=N, including enamine, industrial applications

9.6 Asymmetric oxidations, industrial applications (epoxidation of alkenes & enones, prochiral alcohols, asymmetric dihydroxylation)

9.34 Industrial Applications of Asymmetric Synthesis of Drug Candidates for the Treatment of Hepatitis C

Industrial Applications of Chemo-catalytic C-C, C-N, and C-O Asymmetric Bond Formation

Catalyst Recovery and Recycle; Metal Removal Techniques

Industrial Applications of Hydrolytic Kinetic Resolution

Industrial Applications of Organocatalysis | Stetter, PTC, Benzoin, Baylis-Hillman

Industrial Applications of Biocatalysis. An Overview

Biocatalytic hydrolysis (esters, amides, epoxides, nitriles) & Biocatalytic Dynamic Kinetic Resolution

Industrial Applications of Asymmetric Biocatalytic Reduction including C=O, C=C, and C=N (transaminase)

Industrial Applications of Asymmetric Biocatalytic C-C Bond Forming Reactions

Industrial Applications of Emerging Biocatalytic Reactions

Industrial Applications of Asymmetric Synthesis using Cross-Linked Enzyme Aggregates

Crystallization as a Tool in Industrial Applications of Asymmetric Synthesis

Industrial Applications of Chiral Chromatography

Process Analytics Techniques & Applications in an Industrial Setting

Case study. Aliskiren synthesis (several routes)

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Comprehensive Chirality
 
 

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