Lewis Acid Reagents A Practical Approach

Title :          Lewis Acid Reagents A Practical Approach
Editor :        HISASHI YAMAMOTO
Edition :      1st,illustrated
Publisher :   Oxford University Press
Length :         274 pages
Size :             3.28 MB

Book Description:

A clear and comprehensive laboratory manual providing step-by-step protocols for using Lewis acid reagents to catalyze organic synthesis processes. After an examination of the synthetic utility of bulky aluminum reagents as Lewis acid receptors, the manual covers the following reagents, protocols, and processes: Boron; Magnesium (II) and other alkali and alkaline earth metals; Zinc (II); Chiral titanium complexes for enantioselective catalysis; Tin Lewis acid; Silicon (IV); Silver and gold; Zr- and Hf-centered Lewis acid in organic synthesis; Scandium (III) and yttrium (III); Lanthanides (III); and other transition metal reagents. Also covered are Lewis acid-assisted anionic polymerizations for synthesis of polymers with controlled molecular weights. Lewis Acid Chemistry: A Practical Approach, a volume in the Oxford Practical Approach Series in Chemistry will prove a handy addition to the professional libraries of organic chemists in research and industry.

Lewis acid reagents: a practical approach

Author(s): Hisashi Yamamoto

Publisher: Oxford University Press, Year: 1999

ISBN: 0198500998

[PDF] Lewis Acid Reagents A Practical Approach Table Of Contents

Front Matter……Page 1
List of Contributors……Page 6
Preface……Page 5
Table of Contents……Page 8
1. Introduction……Page 13
2.1 Introduction……Page 17
2.2.1 Amphiphilic Carbonyl Alkylations……Page 18
2.2.2 Amphiphilic Conjugate Alkylations……Page 22
2.2.3 Amphiphilic Conjugate Allylations……Page 24
2.3 Regio- and Stereocontrolled Diels-Alder Reaction……Page 27
2.4 Asymmetric Hetero-Diels-Alder Reaction……Page 28
2.5 Claisen Rearrangement……Page 33
2.6 Epoxide Rearrangement……Page 35
References……Page 40
3.1 Introduction……Page 42
3.2.1 Tris(Pentafluorophenyl)Boron as an Efficient, Air Stable, and Water-Tolerant Lewis Acid Catalyst……Page 43
3.2.2 Diarylborinic Acids as Efficient Catalysts for Selective Dehydration of Aldols……Page 46
3.2.3 3,4,5-Trifluorophenylboronic Acid as an Amidation Catalyst……Page 48
3.3.1 Catalytic Enantioselective Carbo-Diels-Alder Reactions……Page 50
3.3.2 Catalytic Enantioselective Aldol and Allylation Reactions……Page 62
3.3.3 Asymmetric Reactions of Imines Mediated by Chiral Boron Reagents……Page 68
References……Page 72
4.2 Cycloaddition Reactions……Page 75
4.3 Aldol Additions, Allylations, and Other Reactions……Page 81
References……Page 84
5.2 Scope and Limitations……Page 86
References……Page 97
6.1 Introduction……Page 101
6.2 Carbonyl Addition Reaction……Page 104
6.3 Carbonyl-Ene Reaction……Page 109
6.4 Asymmetric Catalytic Desymmetrization……Page 113
6.5 Kinetic Optical Resolution……Page 114
6.6 Positive Non-Linear Effect of Non-Racemic Catalysts……Page 115
6.7 Enantiomer-Selective Activation of Racemic Catalysts……Page 116
6.8 Ene Cyclization……Page 119
6.9 Aldol Reaction……Page 121
6.10 (Hetero) Diels-Alder Reaction……Page 126
6.11 Cyanohydrine Formation……Page 137
6.12 Miscellaneous Reactions……Page 138
References……Page 139
7.1 Introduction……Page 145
7.2.2 Asymmetric Aldol Reactions of Silyl Enol Ethers Derived from Acetic and Propionic Acid Derivatives……Page 146
7.2.3 Asymmetric Synthesis of 2-Substituted Malate Derivatives……Page 148
7.2.4 Asymmetric Synthesis of Syn- and Anti-1,2 Diol Derivatives……Page 151
7.2.5 Catalytic Asymmetric Aldol Reactions……Page 155
7.3 Asymmetric Cyanation Reaction……Page 159
7.4 Asymmetric Protonation……Page 161
References……Page 163
8.1 Introduction……Page 166
8.2 Carbon-Oxygen and Carbon-Nitrogen Bond Formation……Page 167
8.3 Carbon-Carbon Bond Formation……Page 168
8.4 Carbon-Hydrogen Bond Formation……Page 171
References……Page 174
9.2 Enantioselective Aldol Reactions of Activated Isocyanides and Aldehydes……Page 176
9.3 Enantioselective Aldehyde Allylation with Allyltin Reagents Catalysed by a Silver(I)-Phosphine Complex……Page 180
References……Page 182
10.2 Activation of C-F Bond……Page 184
10.3 Activation of Ethers……Page 186
10.4 Carbonyl Activation……Page 187
10.5 Reductive Coupling of Allenes and Alkynes……Page 189
References……Page 191
11.2.1 Friedel-Crafts Reaction……Page 192
11.2.2 Acetalization……Page 196
11.2.3 Acetylation and Esterification of Alcohol……Page 197
11.2.4 Allylation of Carbonyl Compounds with Tetra-Allyltin Catalysed by Scandium(III) Triflate……Page 199
11.2.5 Scandium(III) Triflate-Catalysed Mukaiyama Aldol Reaction……Page 201
11.2.6 Diels-Alder Reaction……Page 203
11.3 Cyclopentadienyl Yttrium Hydride……Page 206
References……Page 207
12.2 Cerium(III) Reagents……Page 209
12.3 Europium(III) Reagents……Page 214
12.4 Ytterbium(III) Reagents……Page 220
12.5 Lanthanum(III) Reagents……Page 223
12.6 Other Lanthanide(III) Reagents……Page 225
References……Page 227
13.2 Activation of Haloalkanes and Carbonyl Compounds……Page 230
13.3.1 Achiral Transition-Metal Catalysts……Page 233
13.3.2 Chiral Transition-Metal Catalysts……Page 234
13.4 Asymmetric Aldol Condensations……Page 243
References……Page 247
14.1 Introduction……Page 249
14.2 Principle, Scope, and Limitations of ‘Lewis Acid-Assisted High-Speed Living Anionic Polymerization’……Page 251
References……Page 264


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