eBook Comprehensive Chirality, 1st Edition

  • Hisashi Yamamoto
  • Erick Carreira
  • Published By:
  • ISBN-10: 0080951686
  • ISBN-13: 9780080951683
  • DDC: 572.8
  • Grade Level Range: College Freshman - College Senior
  • 5648 Pages | eBook
  • Original Copyright 2013 | Published/Released September 2013
  • This publication's content originally published in print form: 2013
  • Price:  Sign in for price

About

Overview

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

Table of Contents

Front Cover.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Introduction: The Importance of Chirality in Drugs and Agrochemicals.
2: Importance of Chirality in the Field of Anti-Infective Agents.
3: Chirality in Antibacterial Agents.
4: Diastereomers, Enantiomers and Bioactivity. TMC207: A New Candidate for the Treatment of Tuberculosis.
5: Fluorine in Medicinal Chemistry: Importance of Chirality.
6: Peptides and Chirality Effects on the Conformation and the Synthesis of Medicinally Relevant Peptides.
7: Stereochemical Lability in Drug Molecules: Cases where Chirality may not be Critical for Drug Development.
8: Chirality in Agrochemicals.
9: The Use of New Phosphines as Powerful Tools in Asymmetric Synthesis of Biologically Active Compounds.
10: Chirality and Combinatorial Libraries for Drug Discovery, An Overview.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Introductory Remarks: Chiral Pool Syntheses and Diastereoselective Reactions.
2: General Principles of Diastereoselective Reactions: Rigid Templates.
3: General Principles of Diastereoselective Reactions: Diastereoselectivity via Substrate-Directable Reactions (Internal Delivery) and Heterocyclizations.
4: General Principles of Diastereoselective Reactions: Acyclic Control of Diastereoselectivity.
5: General Principles of Diastereoselective Reactions: Diastereoselective Domino Reactions.
6: Chiral Pool Synthesis: From α-Amino Acids and Derivatives.
7: Chiral Pool Synthesis: Starting from Terpenes.
8: Chiral Pool Synthesis: Chiral Pool Syntheses Starting from Carbohydrates.
9: Chiral Pool Synthesis: Chiral Pool Syntheses from cis-Cyclohexadiene Diols.
10: Chiral Pool Synthesis: Chiral Pool Synthesis from Hydroxy Acids: Lactic Acid, Tartaric Acid, Malic Acid, and 2-Methyl-3-Hydroxypropionic Acid.
11: Chiral Pool Synthesis: Chiral Pool Synthesis from Quinic Acid.
12: Selected Diastereoselective Reactions: Additions of Achiral Carbanions to Chiral Aldehydes and Ketones.
13: Selected Diastereoselective Reactions: Aldoltype Additions.
14: Selected Diastereoselective Reactions: Enolate Alkylation.
15: Selected Diastereoselective Reactions: Substrate Controlled Stereoselective Conjugate Addition Reactions with Organocopper Reagents.
16: Selected Diastereoselective Reactions: Free Radical Additions and Cyclizations.
17: Selected Diastereoselective Reactions: Intramolecular Diels–Alder Reactions.
18: Selected Diastereoselective Reactions: Diastereoselective Intra- and Intermolecular 1,3-Dipolar Cycloadditions in Natural Product Synthesis.
19: Selected Diastereoselective Reactions: Electrocyclizations.
20: Selected Diastereoselective Reactions: Ionic and Zwitterionic Cyclizations.
21: Selected Diastereoselective Reactions: Diastereoface-Differentiating Claisen, Cope, and [2,3]-Wittig Rearrangements in Contemporary Natural Product Synthesis.
22: Selected Diastereoselective Reactions: Heck Type Cyclizations.
23: Selected Diastereoselective Reactions: Gold Catalyzed Cyclizations.
24: Selected Diastereoselective Reactions: C–H Insertions.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Amino Acid Derived Auxiliaries: Amino Acids as Chiral Auxiliaries.
2: Amino Acid Derived Heterocyclic Chiral Auxiliaries: The Use of Oxazolidinones, Oxazolidinethiones, Thiazolidinethiones, and Imidazolidinones.
3: Terpene Derived Auxiliaries: Camphor and Pinene Derived Auxiliaries.
4: Terpene Derived Auxiliaries: Menthol and Pulegone Derived Auxiliaries.
5: Terpene Derived Auxiliaries: Miscellaneous Terpene Derived Auxiliaries.
6: Acetogenin (Polypriopionate) Derived Auxiliaries: Tartaric Acid.
7: Acetogenin (Polypriopionate) Derived Auxillaries: Hydroxyacids.
8: Acetogenin (Polypriopionate) Derived Auxillaries: Hydroxyacid Derivatives.
9: Alkaloid Derived Auxiliaries: Cinchona Alkaloids and Derivatives.
10: Alkaloid-Derived Auxiliaries: Ephedra Alkaloids.
11: Alkaloid Derived Auxiliaries: Miscellaneous Alkaloids.
12: Carbohydrate Derived Auxiliaries: Mono (and Disaccharide) Derivatives.
13: Carbohydrate Derived Auxiliaries: Amino Sugar and Glycosylamine Auxiliaries.
14: Synthetically Derived Chiral Auxiliaries: Uses of Derivatives of Non-Carbohydrate Aldehydes and Ketones in Asymmetric Synthesis.
15: Non-Chiral Pool Derived Synthetic Auxiliaries: Use of C2-Symmetric Chiral Diols.
16: Synthetically Derived Auxiliaries: Amines (Including Diamines), Hydrazines and Hydroxylamines, and Amino Alcohols.
17: Synthetically Derived Auxiliaries: Phosphorus Derivatives.
18: Synthetically Derived Auxiliaries: Sulfur Derivatives (Including Sulfilamines and Sulfoximines).
19: Synthetically Derived Auxiliaries: Organometallic Derivatives (Main Group and Transition Metals).
20: Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Lithium.
21: Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Magnesium and Calcium.
22: Chiral Ligation for Boron and Aluminum in Stoichiometric Asymmetric Synthesis.
23: Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Silicon.
24: Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Tin and Stannanes.
25: Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Zinc.
26: Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Chromium.
27: Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Titanium and Zirconium Complexes.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Introduction: General Concepts.
2: C–C Bond-Forming Reactions via the Heck Reaction.
3: C–C Bond-Forming Reactions via Cross-Coupling.
4: C–C Bond Formation (Metathesis).
5: C–C Bond Formation by Metal-Catalyzed Asymmetric Allylic Alkylation.
6: C–C Bond Formation (Metal-Catalyzed Reductive Aldol Coupling).
7: C–C Bond Formation (Transition Metal-Catalyzed Michael).
8: C–C Bond Formation (Metal-Carbene Catalyzed).
9: C–C Bond Formation Using Lewis Acids and Silicon Enolates.
10: Enantioselective Aldol Reactions Catalyzed by Chiral Lewis Bases.
11: C–C Bond-Forming Reactions via Transmetallation Using Silyl Enol Ethers.
12: Direct C–C Bond Formation (Henry, aza-Henry).
13: Direct C–C Bond Formation (Michael, Aldol, and Mannich).
14: Reactions Using Thioamide and Allylic Cyanide.
15: C–C Bond Formation.
16: Enantioselective Cyanation of Carbonyls and Imines.
17: Asymmetric 1,2-Addition of Organometallics to Carbonyl and Imine Groups.
18: C–C Bond Formation (1,2-Alkenylation).
19: To Catalytic Asymmetric 1,2-Alkynylation.
20: Other C–C Bond Formations Including Au.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Asymmetric Baeyer–Villiger Oxidation.
2: Oxidation: C–O Bond Formation by C–H Activation.
3: Oxidation: Epoxidation (Allylic Alcohol, Homoallylic Alcohol, Simple C=C, Electron Deficient C=C).
4: Oxidation: α-Hydroxylation of Carbonyls.
5: Oxidation: C–N Bond Formation by Oxidation: C–H Bond Activation.
6: Oxidation: C–N Bond Formation by Oxidation (Aziridines).
7: Oxidation: C–N Bond Formation by Oxidation: Dinitrogen Addition to Double Bond (Diamino).
8: Asymmetric S–O Bond Formation by Oxidation.
9: Oxidation: C–X Bond Formation (X=Halogen, S, Se).
10: Reduction – Hydrogenation: C=C; Chemoselective.
11: Reduction – Hydrogenation: C=O; Chemoselective.
12: Asymmetric Hydrogenation of Prochiral C=N Bonds.
13: Reduction: Hydrosilylation.
14: Reduction: Hydroformylation C–H and C–C.
15: Reduction: Hydrocyanation of C=C.
16: Reduction: Enantioselective Hydrovinylation of Alkenes.
17: Reduction: Pinacol Coupling.
18: Addition Reaction: Kinetic Resolution.
19: Addition Reaction: 1,4 Addition Heteroatom.
20: Addition Reaction: Cycloaddition Involving Oxidation (N=N, N=O; No C–C.
21: Desymmetrization of meso Diols.
22: Desymmetrization of meso Epoxide.
23: Desymmetrization of meso Anhydride.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: C–C Bond Formation: Alkylation.
2: C–C Bond Formation: Michael Reaction.
3: C–C Bond Formation: Mannich Reaction.
4: C–C Bond Formation: Aldol Reaction with Proline Derivatives.
5: C–C Bond Formation: Aldol Reaction with Non-Proline Derivatives.
6: Henry and aza-Henry Reactions.
7: C–C Bond Formation: Cyanation.
8: Allylations of C–O and C–N Double Bonds and Related Reactions.
9: C–C Bond Formation: (aza) Morita–Baylis–Hillman Reaction.
10: C–C Bond Formation: Diels–Alder Reaction.
11: Cyclopropanation Reactions.
12: Benzoin and Stetter Reactions.
13: C–C Bond Formation: Cascade or Domino Reaction.
14: C–N Bond Formation: α-Amination and α-Hydrazination of Carbonyl Compounds with DEAD and Related Compounds.
15: C–N Bond Formation: Aziridine Formation.
16: C–O Bond Formation: α-Oxygenation.
17: C–O Bond Formation: Acylation of meso Diols.
18: C–O Bond Formation: Desymmetrization of Acid Anhydride.
19: C–O Bond Formation: Epoxide Formation.
20: C–X Bond Formation: α-Halogenation of Carbonyl Compounds.
21: C–X Bond Formation: Organocatalytic Enantioselective Halogenation of meso Epoxides.
22: C–X Bond Formation: Organocatalytic α-Sulfenylation and α-Selenenylation.
23: Oxidation: Organocatalyzed Asymmetric Epoxidation of Alkenes.
24: Oxidation: Epoxidation of Enones.
25: Reduction: Asymmetric Transfer Hydrogenation with Hantzsch Esters.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Introduction and General Concepts.
2: Screening Methods for Enzymes.
3: Directed Evolution and (Semi-) Rational Design Strategies for the Creation of Synthetically Useful, Stereoselective Biocatalysts.
4: Cofactor Recycling for Enzyme Catalyzed Processes.
5: Reaction Engineering of Biotransformations.
6: Hydrolysis and Reverse Hydrolysis: Hydrolysis and Formation of Amides.
7: Hydrolysis and Reverse Hydrolysis: Selective Nitrile Hydrolysis Using Nitrilase and Its Related Enzymes.
8: Hydrolysis and Reverse Hydrolysis: Halohydrin Dehalogenases.
9: Hydrolysis and Reverse Hydrolysis: Dynamic Kinetic Resolution.
10: Reduction: Asymmetric Biocatalytic Reduction of Ketones.
11: Reduction: Enantioselective Bioreduction of C–C Double Bonds.
12: Oxidation: Oxidases.
13: Oxidation: Stereoselective Oxidations with Cytochrome P450 Monooxygenases.
14: Oxidation: Asymmetric Enzymatic Sulfoxidation.
15: Oxidation: Haloperoxidases.
16: C–X Bond Formation: Hydroxynitrile Lyases: From Nature to Application.
17: C–X Bond Formation: C–C Bond Formation Using TDP-Dependent Enzymes.
18: C–X Bond Formation: Transaminases as Chiral Catalysts: Mechanism, Engineering, and Applications.
19: C–X Bond Formation: Enzymatic Enantioselective Decarboxylative Protonation and C–C Bond Formation.
20: Multi-Enzyme Reactions.
21: Enzymatic Carbohydrate Synthesis.
22: Enzyme Catalytic Promiscuity: Expanding the Catalytic Action of Enzymes to New Reactions.
23: New Emerging Reactions.
24: Enantioselective Hybrid Catalysts.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Perspective and Concepts: Chirality in Nineteenth Century Science.
2: Perspective and Concepts: Biomolecular Significance of Homochirality: The Origin of the Homochiral Signature of Life.
3: Perspective and Concepts: Overview of Techniques for Assigning Stereochemistry.
4: Physical Separations: Solid-State Forms and Habits of Chiral Substances.
5: Physical Separations: Chiral Discrimination of Enantiomers by Diastereomeric Complexation with Chiral Host Compounds.
6: Physical Separations: Behavior of Structurally Similar Molecules in the Resolution Processes.
7: Chromatographic Separations and Analysis: Chromatographic Separations and Analysis of Enantiomers.
8: Chromatographic Separations and Analysis: Chiral Ion and Ligand Exchange Stationary Phases.
9: Chromatographic Separations and Analysis: Protein and Glycoprotein Stationary Phases.
10: Chromatographic Separations and Analysis: Cyclodextrin Mediated HPLC, GC and CE Enantiomeric Separations.
11: Chromatographic Separations and Analysis: Cellulose and Polysaccharide Derivatives as Stationary Phases.
12: Chromatographic Separations and Analysis: Macrocyclic Glycopeptide Chiral Stationary Phases.
13: Chromatographic Separations and Analysis: Chiral Crown Ether-Based Chiral Stationary Phases.
14: Chromatographic Separations and Analysis: New Stationary Phases.
15: Chromatographic Separations and Analysis: Diastereomeric Derivatization for Chromatography.
16: Chromatographic Separations and Analysis: Chiral Separations by Thin Layer Chromatography.
17: Chromatographic Separations and Analysis: Chiral Gas Chromatography.
18: Chromatographic Separations and Analysis: Supercritical Fluid Chromatography for Chiral Analysis and Semi-Preparative Purification.
19: Chromatographic Separations and Analysis: Chiral Detectors for Chromatography.
20: Spectroscopic Analysis: Polarized Light and Optics.
21: Spectroscopic Analysis: Polarimetry and Optical Rotatory Dispersion.
22: Spectroscopic Analysis: Electronic Circular Dichroism.
23: Spectroscopic Analysis: Synchrotron Radiation Circular Dichroism.
24: Spectroscopic Analysis: Exciton Circular Dichroism for Chiral Analysis.
25: Spectroscopic Analysis: Vibrational Circular Dichroism.
26: Spectroscopic Analysis: Raman Optical Activity.
27: Spectroscopic Analysis: Ab initio Calculation of Chiroptical Spectra.
28: Spectroscopic Analysis: NMR and Shift Reagents.
29: Spectroscopic Analysis: Diastereomeric Derivatization for Spectroscopy.
30: Spectroscopic Analysis: Chiroptical Sensors.
31: Physical and Spectrometric Analysis: An Overview of Chiral Physical Analysis.
32: Physical and Spectrometric Analysis: Anomalous Scattering Single Crystal X-Ray Diffraction.
33: Physical and Spectrometric Analysis: Absolute Configuration Determination by X-Ray Crystallography.
34: Physical and Spectrometric Analysis: Nano-Detection of Chirality.
Half Title Page.
Title Page.
Copyright Page.
Contributors.
Contents.
Preface.
1: Introduction to Industrial Applications of Asymmetric Synthesis.
2: Asymmetry in the Plant: Concepts and Principles for the Scale-Up of Asymmetric Organic Reactions.
3: Industrial Applications of Asymmetric Synthesis: Asymmetric Synthesis as an Enabler of Green Chemistry.
4: Industrial Applications of Asymmetric Reduction of C=C Bonds.
5: Industrial Application of the Asymmetric Reduction of C=O and C=N Bonds, Including Enamides and Enamines.
6: Industrial Applications of Asymmetric Oxidations.
7: Industrial Applications of the Jacobsen Hydrolytic Kinetic Resolution Technology.
8: Industrial Applications of Metal–Promoted C–C, C–N, and C–O Asymmetric Bond Formations.
9: Catalyst Recovery and Recycle: Metal Removal Techniques.
10: Industrial Applications of Organocatalysis.
11: Industrial Applications of Biocatalysis: An Overview.
12: Industrial Applications of Biocatalytic Hydrolysis (Esters, Amides, Epoxides, Nitriles) and Biocatalytic Dynamic Kinetic Resolution.
13: Industrially Relevant Enzymatic Reductions.
14: Industrial Applications of Asymmetric Biocatalytic C–C Bond Forming Reactions.
15: Industrial Applications of Asymmetric Synthesis Using Cross-Linked Enzyme Aggregates.
16: Crystallization as a Tool in Industrial Applications of Asymmetric Synthesis.
17: Industrial Applications of Chiral Chromatography.
18: Industrial Applications of Process Analytical Technology to Asymmetric Synthesis.
19: Synthesis of the Leading HCV Protease Inhibitors.
Index.