Catalysts for Fine Chemical Synthesis, Volume 5, Regio- and Stereo-Controlled Oxidations and Reductions,

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  • Format: eBook
  • Copyright: 2007-10-01
  • Publisher: Wiley-Interscience
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Volume 5 in the Catalysts for Fine Chemical Synthesis series describes new procedures for the regio- and stereo-controlled transformations of compounds involving oxidation or reduction reactions. It describes a wide range of catalysts, including organometallic systems, biocatalysts and biomimetics. This volume also includes descriptions of a variety of conversions, including: Baeyer-Villiger oxidations; Epoxidation reactions; Hydroxylation reactions; Oxidation of alcohols to aldehydes, ketones and carboxylic acids; Reduction of ketones; and Reduction of alkenes including α, β-unsaturated carbonyl compounds. The book will be an important text for practising synthetic organic chemists in industry and academia. Protocols are written in a standard format by the authors who have discovered them Hints, tips and safety advice (where appropriate) is given to ensure that the procedures are reproducible Indications are given as to the range of starting materials used and, where appropriate, comparisons to alternative methodology Includes relevant references to the primary literature.

Table of Contents

Industrial Catalysts for Regio- or Stereo- selective Oxidations and Reductions
A Review of Key Technologies and Targets
Asymmetric Hydrogenation of Alkenes, Enones, Ene-esters and Ene-Acids
(S)-2,2'- Bis{[di(4-methoxyphenyl)phosphinyl]oxy}-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl as a Ligand for Rhodium-Catalysed Asymmetric Hydrogenation
Synthesis and Application of Phosphinite Oxazoline Iridium Complexes for the Asymmetric Hydrogenation of Alkenes
Synthesis and Application of Heterocyclic Phosphine Oxazoline (HetPHOX) Iridium Complexes for the Asymmetric Hydrogenation of Alkenes
(R)-2,2',6,6'- Tetramethoxy-bis[di(3,5-dimethylphenyl)phosphino]-3,3'-bipyridine [(R)-Xyl-P-Phos] as a Ligand for Rhodium-Catalysed Asymmetric Hydrogenation of a-Dehydroamino Acids
Rhodium-Catalysed Asymmetric Hydrogenation of Indoles
Asymmetric Reduction of Ketones
(R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane as a Versatile Ligand for Enantioselective Hydrogenations
Synthesis of Both Enantiomers of 1-Phenylethanol by Reduction of Acetophenone with Geotrichum candidum IFO 5767
Titanocene-Catalysed Reduction of Ketones in the Presence of Water. A Convenient Procedure for the Synthesis of Alcohols by Free-Radical Chemistry
Xyl-TetraPHEMP: A Highly Efficient Biaryl Ligand in the [Diphosphine RuCl2-diamine]-Catalysed Hydrogenation of Simple Aromatic Ketones
N-Arenesulfonyl- and N-Alkylsulfamoyl-1,2-diphenylethylenediamine Ligands for Ruthenium-Catalysed Asymmetric Transfer Hydrogenation of Activated Ketones
The Synthesis and Application of BrXUPHOS: A Novel Monodentate Phosphorus Ligand for the Asymmetric Hydrogenation of Ketones
In Situ Formation of Ligand and Catalyst: Application in Ruthenium-Catalysed Enantioselective Reduction of Ketones
SYNPHOS and DIFLUORPHOS as Ligands for Ruthenium-Catalysed Hydrogenation of Alkenes and Ketones
An Arene Ruthenium Complex with Polymerizable Side-chains for the Synthesis of Immobilised Catalysts
Selective Reduction of Carbonyl Group in beta, gamma- Unsaturated alpha- Ketoesters by Transfer Hydrogenation with Ru-(para-cymene) (TsDPEN)
Preparation of Polymer-Supported Ru-TsDPEN Catalysts and their Use for the Enantioselective Synthesis of (S)-Fluoxetine
Polymer-Supported Chiral Sulfonamide-Catalysed Reduction of B-Keto Nitrile: a Practical Synthesis of (R)-Fluoxetine
Imine Reduction and Reductive Amination
Metal-Free Reduction of Imines: Enantioselective Bronsted Acid-Catalysed Transfer Hydrogenation using Chiral BINOL-Phosphates as Catalysts
Metal-Free Bronsted Acid-Catalysed Transfer Hydrogenation: Enantioselective Synthesis of Tetrahydroquinolines
A Highly Stereoselective Synthesis of 3a-Amino-23,24-bisnor-5a-cholane via Reductive Amination
Oxidation of Primary and Secondary Alcohols
Copper (II)-Catalysed Oxidation of Primary Alcohols to Aldehydes with Atmospheric Oxygen
Solvent-free Dehydrogenation of Secondary Alcohols in the Absence of Hydrogen Abstractors using Robinson's Catalyst
2-Iodoxybenzoic Acid (IBX)/ n-Bu4NBr/ CH2Cl2-H2O: a Mild System for the Selective Oxidation of Secondary Alcohols
Hydroxylation, Epoxidation and Related Reactions
Proline-Catalysed a-Aminoxylation of Aldehydes and Ketones
Ru/ Silica* Cat* TEMPO(c)-Mediated Oxidation of Alkenes to a-Hydroxyacids
Catalytic Enantioselective Epoxidation of trans-Disubstituted and Trisubstituted Alkenes with Arabinose-Derived Ulose
VO(acac)2/ TBHP-Catalysed Epoxidation of 2-(2-Alkenyl)phenols. Highly Regio- and Diastereo-selective Oxidative Cyclisation to 2,3-Dihydrobenzofuranols and 3-Chromanols
An Oxalolidinone Ketone Catalyst for the Asymmetric Epoxidation of cis-Olefins
a-Fluorotropinone Immobilised on Silica: a New Stereoselective Heterogeneous Catalyst for Epoxidation of Alkenes with Oxone
Asymmetric Epoxidation Catalysed by Novel Azacrown Ether-Type Chiral Quaternary Ammonium Salts under Phase-Transfer Catalytic Conditions
Enantioselective Epoxidation of Olefins using Phase-Transfer Conditions and [6-N-((S)-1,2,2-Trimethylpropyl)-5H-dibenz[c,e]azepinium] [rac-TRISPHAT] Salt as Catalyst
Catalytic Asymmetric Epoxidation of a,Unsaturated Esters Promoted by a Yttrium-Biphenyldiol Complex
Catalytic Enantioselective Epoxidation of a,-Enones with a BINOL-Zinc Complex
Asymmetric Epoxidation of Phenyl 2-(3'-Pyridylvinyl) Sulfone using Polyleucine/ Hydrogen Peroxide Gel
Oxidation of Ketones to Lactones or Enones
Synthesis of 2-(Phosphinophenyl)pyridine Ligand and its Application to Palladium-Catalysed Asymmetric Baeyer- Villiger Oxidation of Prochiral Cyclobutanones
(D)-Codeinone from (D)-Dihydrocodeinone via the Use of Modified o-Iodoxybenzoic Acid (IBX)
Oxidative C-C Coupling
Enantioselective Oxidative Coupling of 2-Naphthols Catalysed by a Novel Chiral Vanadium Complex
Catalytic Oxidative Cross-Coupling Reaction of 2-Naphthol Derivatives
Oxidative Coupling of Benzene with a,-Unsaturated Aldehydes by Pd(OAc)2/ HPMoV/ O2 System
Oxidation of Sulfides and Sulfoxides
The First Example of Direct Oxidation of Sulfides to Sulfones by an Osmate- Molecular Oxygen System
Selective Oxidation of Sulfides to Sulfoxides and Sulfones using Hydrogen Peroxide (H2O2) in the Presence of Zirconium Tetrachloride
WO3-30% H2O2-Cinchona Alkaloids: a New Heterogeneous Catalytic System for Asymmetric Oxidation and Kinetic Resolution of Racemic Sulfoxides
Benzyl-4,6-isopropylidene-a-(D)-glucopyranoside, 2-deoxy-2-[[(2-hydroxy-3,5-di-tert-butylphenyl)methylene]amine] as a Ligand for Vanadium-Catalysed Asymmetric Oxidation of Sulfides
Asymmetric Sulfoxidation of Aryl Methyl Sulfides with H2O2 in Water
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