Chirality in Transition Metal Chemistry

Chirality in Transition Metal Chemistry shows how transition metal chirality has an important role in coordination, organometallic and supramolecular systems, and discusses applications in organic synthesis, materials science, and molecular recognition.

Hani, Haniel Amouri, was born in Anapolis Goias (Brazil) and obtained his Ph.D. degree (1987) in chemistry from Universite Louis Pasteur Strasbourg (France), with Professor John A. Osborn, on the subject of homogeneous catalysis (hydrogenation). In 1988 he spent one year at Gif-sur-Yvette (France) as a post-doctoral fellow with Dr Hugh Felkin where he studied C-H activation of saturated hydrocarbon with transition metal polyhydrides. In 1992-1993 he spent one year at UC-Berkeley (USA) with Professor K. Peter C. Vollhardt and was working on the synthesis of oligocyclopentadienyl metal complex and their behaviour as electron transfer reagents. He is a Research Director in CNRS and is currently the director of the 'ARC' group (Auto-assemblage, Reconnaissance et Chiralite) of the IPCM at Universite Pierre et Marie Curie Paris-6. His main research interests are chirality, organometallic and coordination chemistry, and he has had over 90 research papers and reviews published in international scientific journals.

Michel Gruselle was born in Decazeville (France) and obtained his Ph.D. degree (doctorat d'Etat) in the CNRS laboratory of Thiais, a suburb of Paris, in 1975 with Dr Daniel Lefort where he worked on stereochemical problems in radical chemistry. In 1974 he joined Bianca Tchoubar's group and started working on nitrogen activation by organometallic complexes, and he spent some time collaborating with Prof. A.E. Shilov in Moscow. he is a Research Director in CNRS at Universite Pierre et Marie Curie Paris-6 and was the director of the ARC group (Auto-assemblage, Reconnaissance et Chiralite) at the IPCM from 1996-2000. His main research interests a4re enantioselective synthesis in coordination chemistry and in material science and he has had over 110 research papers and reviews published in international scientific journals.

Preface	p. ix
Foreword	p. xi
Introduction	p. 1
References	p. 5
Chirality and Enantiomers	p. 7
Chirality	p. 7
Brief Historical Review	p. 7
Definition of Chirality	p. 13
Definition of a Prochiral Object	p. 17
Definition of Elements of Chirality	p. 19
Principal Elements of Chirality Encountered in Organometallic and Coordination Chemistry	p. 20
Enantiomers and Racemic Compounds	p. 24
Enantiomers	p. 24
Racemic Compounds	p. 24
Diastereomers	p. 27
Enantiomeric and Diastereomeric Excesses	p. 29
Racemization and Configurational Stability	p. 30
Absolute configurations and System Descriptors	p. 32
Definition of the Absolute and Relative Configuration of a Molecule	p. 32
Absolute Configuration and Universal Descriptors	p. 33
Physical Properties of Enantiomers and Racemics	p. 43
Optical Properties	p. 43
Determination of Absolute Configuration	p. 48
Determination of the Enantiomeric Excess (ee)	p. 50
Principles of Resolution and Preparation of Enantiomers	p. 55
Spontaneous Resolution	p. 55
Use of a Chiral Auxiliary	p. 56
Chromatography	p. 57
Enantioselective Synthesis	p. 58
Summary	p. 61
References	p. 61
Some Examples of Chiral Organometallic Complexes and Asymmetric Catalysis	p. 65
Chirality at Metal Half-sandwich Compounds	p. 65
Chiral Three-legged Piano Stool: the CpMnL1L2L3 Model	p. 65
Chiral Three-legged Piano Stool: the CpReL1L2L3 Model	p. 68
Other Related Complexes with Chiral-at-Metal Centre	p. 71
Chiral-at-metal Complexes in Organic Synthesis	p. 75
The Chiral Acyl-Iron Complex	p. 75
The Chiral Cyclic Acyl-Cobalt Complex	p. 79
The Lewis Acid-Rhenium Complex	p. 79
Asymmetric Catalysis by Chiral Complexes	p. 80
Asymmetric Hydrogenation	p. 80
Asymmetric Epoxidation and Dihydroxylation	p. 88
Gold Complexes in Asymmetric Catalysis	p. 89
Asymmetric Nucleophilic Catalysis	p. 91
Summary	p. 94
References	p. 94
Chiral Recognition in Organometallic and Coordination Compounds	p. 99
Octahedral Metal Complexes with Helical Chirality	p. 101
Heterochiral Recognition	p. 101
Homochiral Recognition	p. 102
Chiral Recognition Using Modified Cyclodextrins	p. 103
Chiral Recognition Using the Chiral Anion Strategy	p. 105
Tris(tetrachlorobenzenediolato) Phosphate Anion (TRISPHAT)	p. 105
1,1'-binaphty1-2,2'-diyl Phosphate Anion (BNP)	p. 111
Bis(binaphthol) Borate Anion (BNB)	p. 113
Brief Introduction to DNA Discrimination by Octahedral Polypyridyl Metal Complexes	p. 114
Introduction	p. 114
Background on DNA Binding with Chiral Octahedral Metal Complexes- the [Ru(phen) 3]2+ Example	p. 115
Molecular Light Switches for DNA	p. 116
Summary	p. 117
References	p. 117
Chirality in Supramolecular Coordination Compounds	p. 121
Self-assembly of Chiral Polynuclear Complexes from Achiral Building Units	p. 121
Helicates	p. 121
Molecular Catenanes and Knots	p. 129
Chiral Tetrahedra	p. 133
Chiral Anti(prism)	p. 143
Chiral Octahedra and Cuboctahedra	p. 146
Chiral Metallo-macrocycles with Organometallic Half-sandwich Complexes	p. 147
Chirality Transfer in Polynuclear Complexes: Enantioselective Synthesis	p. 153
Chirality Transfer via Resolved Bridging Ligands	p. 154
Chirality Transfer via a Resolved Chiral Auxiliary Coordinated to a Metal or the Use of Resolved Metallo-bricks	p. 162
Summary	p. 172
References	p. 172
Chiral Enantiopure Molecular Materials	p. 179
General Considerations	p. 179
Types of Organization	p. 179
Properties	p. 180
Chiral and Enantiopure Materials	p. 180
Conductors	p. 181
General Considerations	p. 181
Why Enantiopure Molecular conductors?	p. 182
Strategies to Obtain Enantiopure Conductors	p. 183
Metallomesogens	p. 189
General Considerations	p. 189
Metallomesogens with the Chiral Element Attached Driectly to the Metal	p. 189
Metallomesogens with the Chiral Element (s) in the Ligands	p. 190
Metallomesogens Where the Metal and Ligands Generate Helical Chirality	p. 193
Metallomesogens Based on Chiral Phthalocyanines	p. 199
Porous Metalorganic Coordination Networks (MOCN)	p. 204
General Considerations	p. 204
Main Strategies to Obtain Enantiopure MOCNs	p. 205
1D MOCNs	p. 206
2D and 3D MOCNs	p. 209
Molecular Magnets	p. 215
Why Enantiopure Molecular Magnets?	p. 215
Strategies and Synthesis	p. 216
Enantioselective Synthesis or Resolution of Chiral Ligands	p. 216
Chiral Inductive Effect of Resolved Building Blocks in the Formation of Supramolecular Structures	p. 218
Chiral Inductive Effect of Resolved Templates	p. 222
Chiral Surfaces	p. 224
General Considerations	p. 224
Spontaneous Resolution of Chiral Molecules at a Metal Surface in 2D Space	p. 225
Induction of Chirality by Enantiopure Chiral Molecules in 3D, Resulting in Enantiopure Structures at Metal Surfaces	p. 228
Formation of Chiral Metal Surfaces by Electrodeposition in the Presence of a Chiral Ionic Medium	p. 229
Formation of Chiral Nanoparticles	p. 229
Summary	p. 232
References	p. 233
Index	p. 239
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Chirality in Transition Metal Chemistry Molecules, Supramolecular Assemblies and Materials

Summary

Author Biography

Table of Contents

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