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

Stanley M. Roberts (Editor), John Whittall (Editor)
ISBN: 978-0-470-09022-0
336 pages
September 2007
Catalysts for Fine Chemical Synthesis, Volume 5, Regio- and Stereo-Controlled Oxidations and Reductions (0470090227) cover image
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.
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CHAPTER 1: Industrial Catalysts for Regio- or Stereo- selective Oxidations and Reductions. A Review of Key Technologies and Targets.
J. Whittall

CHAPTER 2: Asymmetric Hydrogenation of Alkenes, Enones, Ene-esters and Ene-Acids

2.1: (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
I. Gergely, C. Hegeds and J. Bakos.

2.2: Synthesis and Application of Phosphinite Oxazoline Iridium Complexes for the Asymmetric Hydrogenation of Alkenes
F. Menges and A. Pfaltz.

2.3: Synthesis and Application of Heterocyclic Phosphine Oxazoline (HetPHOX) Iridium Complexes for the Asymmetric Hydrogenation of Alkenes
F. Menges and P.G. Cozzi.

2.4: (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
J. Wu and A.S.C. Chan.

2.5: (R,R)-2,3-Bis(tert-butylmethylphosphine)quinoxaline (Quinox P*) as a Ligand for Rhodium-Catalysed Asymmetric Hydrogenation of Prochiral Amino Acid and Amine Derivatives
T. Imamoto and A. Koide.

2.6: Rhodium-Catalysed Asymmetric Hydrogenation of Indoles
R. Kuwano and M. Sawamura.

CHAPTER 3: Asymmetric Reduction of Ketones

3.1: (R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane as a Versatile Ligand for Enantioselective Hydrogenations
N. Dubrovina and A. Borner.

3.2: Synthesis of Both Enantiomers of 1-Phenylethanol by Reduction of Acetophenone with Geotrichum candidum IFO 5767
K. Nakamura, M. Fujii and Y. Ida.

3.3: Titanocene-Catalysed Reduction of Ketones in the Presence of Water. A Convenient Procedure for the Synthesis of Alcohols by Free-Radical Chemistry
A. Rosales, J.M. Cuerva and J.E. Oltra.
3.4: Xyl-TetraPHEMP: A Highly Efficient Biaryl Ligand in the [Diphosphine RuCl2-diamine]-Catalysed Hydrogenation of Simple Aromatic Ketones
P.H. Moran, J.P. Henschke, A. Zanotti-Gerosa and I C. Lennon.

3.5: N-Arenesulfonyl- and N-Alkylsulfamoyl-1,2-diphenylethylenediamine Ligands for Ruthenium-Catalysed Asymmetric Transfer Hydrogenation of Activated Ketones
M.S. Stephan and B. Mohar.

3.6: The Synthesis and Application of BrXUPHOS: A Novel Monodentate Phosphorus Ligand for the Asymmetric Hydrogenation of Ketones
M. Wills, Y. Xu, G. Docherty and G. Woodward.

3.7: In Situ Formation of Ligand and Catalyst: Application in Ruthenium-Catalysed Enantioselective Reduction of Ketones
J. Wettergren and H. Adolfsson.

3.8: SYNPHOS and DIFLUORPHOS as Ligands for Ruthenium-Catalysed Hydrogenation of Alkenes and Ketones
S. Jeulin, V. Ratovelomanana-Vidal and J-P. Genet.

3.9: An Arene Ruthenium Complex with Polymerizable Side-chains for the Synthesis of Immobilised Catalysts
E. Burri, S.B. Wendicke, K. Severin.

3.10: Selective Reduction of Carbonyl Group in beta, gamma- Unsaturated alpha- Ketoesters by Transfer Hydrogenation with Ru-(para-cymene) (TsDPEN)
M. Guo, D. Li, Y. Sun and Z. Zhang.

3.11: Preparation of Polymer-Supported Ru-TsDPEN Catalysts and their Use for the Enantioselective Synthesis of (S)-Fluoxetine
L. Chai, Y. Li and Q. Wang.

3.12: Polymer-Supported Chiral Sulfonamide-Catalysed Reduction of B-Keto Nitrile: a Practical Synthesis of (R)-Fluoxetine
G.Wang and G. Zhao.

CHAPTER 4: Imine Reduction and Reductive Amination

4.1: Metal-Free Reduction of Imines: Enantioselective Bronsted Acid-Catalysed Transfer Hydrogenation using Chiral BINOL-Phosphates as Catalysts
M. Rueping, E. Sugiono, C. Azap and T. Theissmann.

4.2: Metal-Free Bronsted Acid-Catalysed Transfer Hydrogenation: Enantioselective Synthesis of Tetrahydroquinolines
M. Rueping , T. Theissmann and A. P. Antonchick.

4.3: A Highly Stereoselective Synthesis of 3a-Amino-23,24-bisnor-5a-cholane via Reductive Amination
S. N. Khan, N.J. Cho and H-S. Kim.

CHAPTER 5: Oxidation of Primary and Secondary Alcohols

5.1: Copper (II)-Catalysed Oxidation of Primary Alcohols to Aldehydes with Atmospheric Oxygen
S. Jammi and T. Punniyamurthy.

5.2: Solvent-free Dehydrogenation of Secondary Alcohols in the Absence of Hydrogen Abstractors using Robinson's Catalyst
G.B.W.L. Ligthart, R.H. Meijer, J. v. Buijtenen, J. Meuldijk, J.A.J.M. Vekemans and L. A. Hulshof.

5.3: 2-Iodoxybenzoic Acid (IBX)/ n-Bu4NBr/ CH2Cl2-H2O: a Mild System for the Selective Oxidation of Secondary Alcohols
K. Kittigowittana, M. Pohmakotr, V. Reutrakul and C. Kuhakarn.

CHAPTER 6: Hydroxylation, Epoxidation and Related Reactions

6.1: Proline-Catalysed a-Aminoxylation of Aldehydes and Ketones
Y. Hayashi and M. Shoji.

6.2: Ru/ Silica* Cat* TEMPO(c)-Mediated Oxidation of Alkenes to a-Hydroxyacids
R. Ciriminna and M. Pagliaro.

6.3: Catalytic Enantioselective Epoxidation of trans-Disubstituted and Trisubstituted Alkenes with Arabinose-Derived Ulose
T.K. M. Shing, G.Y.C. Leung and T. Luk.

6.4: 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
A. Lattanzi and A. Scettri.

6.5: An Oxalolidinone Ketone Catalyst for the Asymmetric Epoxidation of cis-Olefins
D. Goeddel and Y. Shi.

6.6: a-Fluorotropinone Immobilised on Silica: a New Stereoselective Heterogeneous Catalyst for Epoxidation of Alkenes with Oxone
G. Sartori, A. Armstrong, R. Maggi, A. Mazzacani, R. Sartorio, F. Bigi and B. Dominguez-Fernandez.

6.7: Asymmetric Epoxidation Catalysed by Novel Azacrown Ether-Type Chiral Quaternary Ammonium Salts under Phase-Transfer Catalytic Conditions
K. Hori, K. Tani, and Y. Tohda.

6.8: 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
J. Vachon, C. Perollier, A. Martinez and J. Lacour.

6.9: Catalytic Asymmetric Epoxidation of a,Unsaturated Esters Promoted by a Yttrium-Biphenyldiol Complex
M. Shibasaki, H. Kakei and S. Matsunaga..

6.10: Catalytic Enantioselective Epoxidation of a, -Enones with a BINOL-Zinc Complex
A. Minatti and K.H. Dotz

6.11: Asymmetric Epoxidation of Phenyl 2-(3'-Pyridylvinyl) Sulfone using Polyleucine/ Hydrogen Peroxide Gel
M. Pitts and J. Whittall.

CHAPTER 7: Oxidation of Ketones to Lactones or Enones

7.1: Synthesis of 2-(Phosphinophenyl)pyridine Ligand and its Application to Palladium-Catalysed Asymmetric Baeyer- Villiger Oxidation of Prochiral Cyclobutanones
K. Ito and T. Katsuki.

7.2: (D)-Codeinone from (D)-Dihydrocodeinone via the Use of Modified o-Iodoxybenzoic Acid (IBX)
P. Mather and J. Whittall.

CHAPTER 8: Oxidative C-C Coupling

8.1: Enantioselective Oxidative Coupling of 2-Naphthols Catalysed by a Novel Chiral Vanadium Complex
N-S. Xie, Q-Z. Liu, Z-B. Luo, L-Z. Gong, A-Q. Mi and Y-Z. Jiang.

8.2: Catalytic Oxidative Cross-Coupling Reaction of 2-Naphthol Derivatives
S. Habaue and T. Temma.

8.3: Oxidative Coupling of Benzene with a,-Unsaturated Aldehydes by Pd(OAc)2/ HPMoV/ O2 System
T. Yamada, S. Sakaguchi and Y. Ishii.

CHAPTER 9: Oxidation of Sulfides and Sulfoxides

9.1: The First Example of Direct Oxidation of Sulfides to Sulfones by an Osmate- Molecular Oxygen System
B.M. Choudary, C. Reddy, V. Reddy, B.V. Prakash, M.L. Kantam and B. Sreedhar.

9.2: Selective Oxidation of Sulfides to Sulfoxides and Sulfones using Hydrogen Peroxide (H2O2) in the Presence of Zirconium Tetrachloride
K. Bahrami.

9.3: WO3-30% H2O2-Cinchona Alkaloids: a New Heterogeneous Catalytic System for Asymmetric Oxidation and Kinetic Resolution of Racemic Sulfoxides
V. V. Thakur and A. Sudalai.

9.4: 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
R. Del Litto, G. Roviello and F. Ruffo.

9.5: Asymmetric Sulfoxidation of Aryl Methyl Sulfides with H2O2 in Water
A. Scarso and G. Strukul

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