Catalysts for Fine Chemical Synthesis, Volume 5, Regio- and Stereo-Controlled Oxidations and Reductions
- 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.
CHAPTER 2: Asymmetric Hydrogenation of Alkenes, Enones, Ene-esters and Ene-Acids
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.
[(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
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
M.S. Stephan and B. Mohar.
3.6: The Synthesis and Application of BrXUPHOS: A Novel
Monodentate Phosphorus Ligand for the Asymmetric Hydrogenation of
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
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
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
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
Y. Hayashi and M. Shoji.
6.2: Ru/ Silica* Cat* TEMPO(c)-Mediated Oxidation of Alkenes to
R. Ciriminna and M. Pagliaro.
6.3: Catalytic Enantioselective Epoxidation of
trans-Disubstituted and Trisubstituted Alkenes with
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
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
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
[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
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
9.3: WO3-30% H2O2-Cinchona Alkaloids: a New Heterogeneous
Catalytic System for Asymmetric Oxidation and Kinetic Resolution of
V. V. Thakur and A. Sudalai.
a Ligand for Vanadium-Catalysed Asymmetric Oxidation of
R. Del Litto, G. Roviello and F. Ruffo.
9.5: Asymmetric Sulfoxidation of Aryl Methyl Sulfides with H2O2
A. Scarso and G. Strukul