Regio- and Stereo-Controlled Oxidations and Reductions, Volume 5 (eBook, PDF)

Redaktion: Roberts, Stanley M.; Whittall, John

• Format: PDF

Produktbeschreibung

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 alpha, beta-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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Produktdetails

• Verlag: John Wiley & Sons
• Erscheinungstermin: 20. August 2007
• Englisch
• ISBN-13: 9780470090237
• Artikelnr.: 37290503

Autorenporträt

Bryan and Ellie Stockton hope they left behind their demons when they move to their idyllic new home in southern West Virginia. Above all, they want a fresh start for their young son, Derrick, who witnessed the tumultuous first years of their marriage - years that were rife with substance abuse, rage, and resentment. Their bright hope for the future is darkened when a child disappears from their neighborhood. The couple becomes suspicious of a reclusive resident with a degenerative brain disorder. Strange events begin to happen in their house just as Derrick tells them about a new friend who visits him at night. Their son might be acting out from trauma he endured, or he could be the obsession of something much more sinister.

Inhaltsangabe

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