Organosulfur chemistry in asymmetric synthesis:
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Weinheim
WILEY-VCH
2008
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| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XVI, 432 S. graph. Darst. |
| ISBN: | 9783527318544 3527318542 |
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| 245 | 1 | 0 | |a Organosulfur chemistry in asymmetric synthesis |c ed. by Takeshi Toru ... |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2008 | |
| 300 | |a XVI, 432 S. |b graph. Darst. | ||
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| 650 | 4 | |a Asymmetric synthesis | |
| 650 | 4 | |a Enantioselective catalysis | |
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I V
Contents
Preface XI
ListofContributors XIII
1 Asymmetrie Synthesis of Chiral Sulfoxides 1
Henri B. Kagan
1.1 Chiral Sulfoxides 3
1.1.1 Introduction 1
1.1.2 The Main Routes to Chiral Sulfoxides 2
1.2 Use of Chiral Sulfur Precursors 3
1.2.1 Sulfinates (Andersen Method) 3
1.2.2 Diastereoselective Formation of Sulfinates 5
1.2.3 Sulfinates from Sulfites 7
1.2.4 Sulfinamides 9
1.3 Catalytic Enantioselective Sulfide Oxidation 12
1.3.1 Titanium Complexes 32
1.3.1.1 Diesters of Tartaric Acid 12
1.3.1.2 C2-Symmetric 1,2-Diols as Ligands 14
1.3.1.3 Binaphthol and Derivatives 35
1.3.1.4 C3-Symmetric Triethanolamine Ligands 35
1.3.1.5 Ti (Sälen) Catalysts 16
1.3.2 Manganese Complexes 17
1.3.3 Vanadium Complexes 38
1.3.4 Molybdenum Complexes 19
1.3.5 Iron Complexes 19
1.3.6 Miscellaneous 20
1.4 Catalytic Arylation of Sulfenate Anions 21
1.5 Enantioselective Oxidation of Sulfides 22
1.6 Summary 25
References 26
Organosulfar Chemistry in Asymmetrie Synthesis. Edited by Takeshi Toru and Carsten Bolm
Copyright © 2008 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-31854-4
VII Contents
2 Asymmetrie Synthesis ofOptically Active Sulfinic Acid Esters 31
Jözef Drabowicz, Piotr Kielbasihski, Dorota Krasowska, and Marion Mikotajczyk
2.1 Introduction 31
2.2 Enantiomeric Sulfinic Acid Esters 32
2.3 Diastereomeric Sulfinic Acid Esters 40
References 53
3 Asymmetrie Transformations Mediated by Sulfinyl Croups 55
Jose L Carc'ia Ruano, Jose Alem'an, M. Beten Cid,
M. Angeles Fernändez-lbänez, M. Carmen Maestro, M. Rosario Martin,
and Ana M. Mart'tn-Castro
3.1 Introduction 55
3.2 Nucleophilic Additions to C=O and C=N Bonds Mediated by
a-Sulfinyl Groups 57
3.2.1 y?-Ketosulfoxides 57
3.2.1.1 Reduction Reactions 57
3.2.1.2 Alkylation Reactions 70
3.2.1.3 Aldol Reaction with /J-Ketosulfoxides Acting as Electrophiles 73
3.2.1.4 Hydrocyanation Reactions 76
3.2.2 /?-Imino(enamino)sulfoxides 79
3.3 Conjugate Additions to a,/?-Unsaturated Sulfoxides 83
3.3.1 Nucleophilic Additions 84
3.3.1.1 (E) and (Z)-2-Substituted Vinyl Sulfoxides 84
3.3.1.2 1-Substituted Vinyl Sulfoxides 88
3.3.2 Tandem Reactions 91
3.3.3 Radical Conjugate Additions and Other Reactions 95
3.4 Cycloadditions 96
3.4.1 Asymmetrie Diels-Alder Reactions 96
3.4.1.1 Sulfinyl Dienophiles 96
3.4.1.2 Sulfinyl Dienes 107
3.4.2 Asymmetrie Hetero Diels-Alder Reactions 109
3.4.3 Asymmetrie 1,3-Dipolar Cycloadditions 111
3.4.3.1 Reactions with Nitrones 111
3.4.3.2 Reactions with Azomethine Ylides 115
3.4.3.3 Reactions with Nitrile Oxides 117
3.4.3.4 Reactions with Diazoalkanes 118
3.4.3.5 Reactions with Other Dipoles 121
3.4.4 Other Asymmetrie Cycloadditions 122
3.5 Asymmetrie Processes Stereocontrolled by Remote Sulfoxides 123
3.5.1 Nucleophilic Processes 123
3.5.1.1 Reactions with Sulfinylated Electrophiles 123
3.5.1.2 Reactions with Sulfinylated Nucleophiles 130
3.6 Asymmetrie Pummerer Reaction 136
References 142
Contents I VII
4 Synthesis and Applications of Chiral Dithioacetal Derivatives 161
Philip C. Bulman Page and Benjamin R. Buckley
4.1 Introduction 161
4.2 Lithiated Dithianes 162
4.3 Alternative Methods 169
4.4 Oxidation Methods for the Construction of Chiral Dithioacetal
Derivatives and Applications in Synthesis 171
4.5 Applications of Chiral Dithioacetal Derivatives in Natural Product
and Biologically Active Compound Synthesis 176
4.6 Summary 177
References 177
5 Synthesis and Use of Chiral Sulfur Ylides 179
Jean-Franqois Briere and Patrick Metzner
5.1 Introduction 179
5.1.1 Reactions of Sulfonium Ylides 179
5.1.2 Methods of Preparation 280
5.1.3 Conditions for Stereocontrol and Theoretical Investigations 182
5.2 Epoxidation Reaction 183
5.2.1 Stoichiometric Use of Sulfides 183
5.2.1.1 Stilbene Oxides 183
5.2.1.2 Unsaturated Epoxides 186
5.2.1.3 Aliphatic Epoxides 186
5.2.1.4 Terminal Epoxides 187
5.2.1.5 Functional Epoxides 187
5.2.2 Catalytic Use of Sulfides 188
5.3 Aziridination 189
5.3.1 Stoichiometric Aziridination, and Mechanism 190
5.3.2 Catalytic Aziridination 192
5.4 Cyclopropanation 194
5.4.1 Stoichiometric Cyclopropanation 195
5.4.2 Catalytic Cyclopropanation 197
5.5 [2,3]-Sigmatropic Rearrangement 199
5.6 Other Reactions 203
5.7 Conclusions 204
References 204
6 Synthesis and Use of Chiral Sulfoximines 209
Christin Worch, Agathe Christine Mayer, and Carsten Bolm
6.1 Introduction 209
6.2 Synthesis and Structural Modification 211
6.3 Applications in Asymmetrie Synthesis 213
6.3.1 Use of Sulfoximines as Chiral Auxiliaries 214
VIIII Contents
6.3.2 Use of Sulfoximines as Chiral Ligands 224
6.4 Condusions 229
References 229
7 Synthesis and Use of Chiral Sulfinamides 233
Chris H. Senanayake, Zhengxu Hart, and Dhileepkumar Krishnamurthy
7.1 Introduction 233
7.2 Synthesis of Chiral Sulfinamides and Chiral Sulfinylimines 234
7.2.1 Background 234
7.2.2 Synthesis of Chiral Sulfinamides 235
7.2.3 Synthesis of Chiral Sulfinylimines 240
7.3 Use of Chiral Sulfinamides 241
7.3.1 Use as Chiral Sulfinyl Auxiliaries 241
7.3.2 Synthesis of Chiral Amines 241
7.3.3 Synthesis of Aziridines 249
7.3.4 Use of Chiral Sulfinamides as Ligands in Catalytic Asymmetrie
Reactions 252
7.3.4.1 Asymmetrie Diels-Alder Reaction 252
7.3.4.2 Asymmetrie Allylic Alkylation Reaction 254
7.3.4.3 Asymmetrie Hydrogenation of Olefins 255
7.3.5 Application of Chiral Sulfinamides in the Synthesis of Biologically
Active Molecules 256
7.3.5.1 Synthesis ofSC-53116 256
7.3.5.2 Total Synthesis of (6R,7S)-7-Amino-7,8-Dihydro-a-Bisabolene 257
7.3.5.3 Asymmetrie Synthesis of (—)-Pateamine 258
7.3.5.4 Synthesis of Polyoxamic Acid Lactone 259
7.3.5.5 Synthesis of Single Enantiomers of Sibutramine and Cetirizine 259
7.4 Summary 261
References 262
8 Asymmetrie Catalysis Using Sulfoxides as Ligands 265
Inmaculada Fernändez and Noureddine Khiar
8.1 Introduction 265
8.2 Some Considerations on the Coordination of Sulfoxides 266
8.3 Sulfoxides as Ligands in Metal-Catalyzed Asymmetrie Catalysis 267
8.3.1 Catalytic Hydrogenations 267
8.3.2 Catalytic Cycloadditions 270
8.3.3 Addition of Diethylzinc to Benzaldehyde 272
8.3.4 Catalytic Allylic Substitutions 273
8.3.5 Utilization of Sulfoxides in Other Metal-Catalyzed Asymmetrie
Processes 279
8.3.5.1 Use of Sulfoxides in Lewis Acid-Lewis Base Bifunctional
Asymmetrie Catalysis 279
Contents I IX
8.3.5.2 Use of Sulfoxides as Chiral Ligands in Combination with Achiral
Catalysts 281
8.3.5.3 Use of Sulfoxides as Ligands in Enantioselective Radical
Allylation 283
8.3.6 Use of Sulfoxides as Neutral Coordinate-Organocatalysts 284
8.4 Condusions 287
References 288
9 Sulfones in Asymmetrie Catalysis 291
Juan Carlos Carretero, Ramön Gömez Arrayäs, and Javier Adrio
9.1 Introduction 291
9.2 Alkenyl Sulfones in Asymmetrie Catalysis 292
9.2.1 Asymmetrie Catalytic Conjugate Addition 292
9.2.2 Asymmetrie Catalytic Conjugate Reduction 297
9.2.3 Asymmetrie Catalytic Radical Addition 298
9.2.4 Asymmetrie Catalytic Cycloadditions 300
9.2.5 Asymmetrie Catalytic Dihydroxylation and Epoxidation Reactions 301
9.3 Ketosulfones 305
9.3.1 Asymmetrie Reduction of Ketosulfones 305
9.3.2 Diels-Alder Reactions 308
9.3.3 Michael-Aldol Reactions 309
9.4 a-Diazo-/?- Ketosulfones 311
9.5 Miscellaneous: Other Substituted Sulfones 314
9.6 Summary 315
References 317
10 Asymmetrie Reaction of a-Sulfenyl Carbanions 321
Shuichi Nakamura and Takeshi Toru
10.1 Asymmetrie Reactions of a-Sulfenyl Carbanions 321
10.1.1 Introduction 321
10.2 Racemization Mechanism and Configurational Stability of a-Sulfenyl
Carbanions 323
10.3 Diastereoselective Reaction of a-Sulfenyl Carbanions 326
10.4 Enantioselective Reaction of a-Sulfenyl Carbanions 329
10.4.1 Reaction Pathway of Enantioselective Reaction of a-Sulfenyl
Carbanions 329
10.4.2 Enantioselective Reactions of a-Sulfenyl Carbanions 332
10.4.3 Enantioselective Reactions of a-Lithiated Dithioacetals 344
10.5 Conclusions 346
References 347
X I Contents
11 Stereoselective Reactions with a-Sulfinyl Carbanions 351
Alessandro Volonterio and Matteo Zanda
11.1 Introduction 351
11.2 Stereochemistry of oc-Sulfinyl Carbanions 352
11.3 Alkylation of a-Sulfinyl Carbanions 354
11.4 Conjugated Additions with a-Sulfinyl Carbanions 357
11.5 Additions of a-Sulfinyl Carbanions to Carbonyl Compounds 360
11.6 Additions of a-Sulfinyl Carbanions to Imines and Related
Compounds 367
11.7 Conclusions 371
References 372
12 Asymmetrie Reactions of or-Sulfonyl Carbanions 375
Hans-Joachim Cais
12.1 Introduction 375
12.2 Configurationally Stable a-Sulfonyl Carbanions 380
12.3 Configurationally Labile a-Sulfonyl Carbanions 382
12.4 Configurationally Labile a-Sulfonyl Carbanions with
an Additional Stereogenic Center 388
References 396
13 Computational Studies on Asymmetrie Reactions with
Sulfur Reagents 399
David Balcells and Feliu Maseras
13.1 Introduction 399
13.2 Directing Effect of Chiral Sulfur Substituents 400
13.3 Sulfur Centers in Chiral Intermediates 403
13.4 Synthesis of Chiral Sulfoxides from Prochiral Sulfides 405
13.5 Synthesis of Chiral Sulfoxides from Racemic Precursors 409
13.6 Other Systems Involving Chiral Sulfur Centers 413
13.7 Conclusions and Perspectives 414
References 435
Index 417 |
| adam_txt |
I V
Contents
Preface XI
ListofContributors XIII
1 Asymmetrie Synthesis of Chiral Sulfoxides 1
Henri B. Kagan
1.1 Chiral Sulfoxides 3
1.1.1 Introduction 1
1.1.2 The Main Routes to Chiral Sulfoxides 2
1.2 Use of Chiral Sulfur Precursors 3
1.2.1 Sulfinates (Andersen Method) 3
1.2.2 Diastereoselective Formation of Sulfinates 5
1.2.3 Sulfinates from Sulfites 7
1.2.4 Sulfinamides 9
1.3 Catalytic Enantioselective Sulfide Oxidation 12
1.3.1 Titanium Complexes 32
1.3.1.1 Diesters of Tartaric Acid 12
1.3.1.2 C2-Symmetric 1,2-Diols as Ligands 14
1.3.1.3 Binaphthol and Derivatives 35
1.3.1.4 C3-Symmetric Triethanolamine Ligands 35
1.3.1.5 Ti (Sälen) Catalysts 16
1.3.2 Manganese Complexes 17
1.3.3 Vanadium Complexes 38
1.3.4 Molybdenum Complexes 19
1.3.5 Iron Complexes 19
1.3.6 Miscellaneous 20
1.4 Catalytic Arylation of Sulfenate Anions 21
1.5 Enantioselective Oxidation of Sulfides 22
1.6 Summary 25
References 26
Organosulfar Chemistry in Asymmetrie Synthesis. Edited by Takeshi Toru and Carsten Bolm
Copyright © 2008 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-31854-4
VII Contents
2 Asymmetrie Synthesis ofOptically Active Sulfinic Acid Esters 31
Jözef Drabowicz, Piotr Kielbasihski, Dorota Krasowska, and Marion Mikotajczyk
2.1 Introduction 31
2.2 Enantiomeric Sulfinic Acid Esters 32
2.3 Diastereomeric Sulfinic Acid Esters 40
References 53
3 Asymmetrie Transformations Mediated by Sulfinyl Croups 55
Jose L Carc'ia Ruano, Jose Alem'an, M. Beten Cid,
M. Angeles Fernändez-lbänez, M. Carmen Maestro, M. Rosario Martin,
and Ana M. Mart'tn-Castro
3.1 Introduction 55
3.2 Nucleophilic Additions to C=O and C=N Bonds Mediated by
a-Sulfinyl Groups 57
3.2.1 y?-Ketosulfoxides 57
3.2.1.1 Reduction Reactions 57
3.2.1.2 Alkylation Reactions 70
3.2.1.3 Aldol Reaction with /J-Ketosulfoxides Acting as Electrophiles 73
3.2.1.4 Hydrocyanation Reactions 76
3.2.2 /?-Imino(enamino)sulfoxides 79
3.3 Conjugate Additions to a,/?-Unsaturated Sulfoxides 83
3.3.1 Nucleophilic Additions 84
3.3.1.1 (E) and (Z)-2-Substituted Vinyl Sulfoxides 84
3.3.1.2 1-Substituted Vinyl Sulfoxides 88
3.3.2 Tandem Reactions 91
3.3.3 Radical Conjugate Additions and Other Reactions 95
3.4 Cycloadditions 96
3.4.1 Asymmetrie Diels-Alder Reactions 96
3.4.1.1 Sulfinyl Dienophiles 96
3.4.1.2 Sulfinyl Dienes 107
3.4.2 Asymmetrie Hetero Diels-Alder Reactions 109
3.4.3 Asymmetrie 1,3-Dipolar Cycloadditions 111
3.4.3.1 Reactions with Nitrones 111
3.4.3.2 Reactions with Azomethine Ylides 115
3.4.3.3 Reactions with Nitrile Oxides 117
3.4.3.4 Reactions with Diazoalkanes 118
3.4.3.5 Reactions with Other Dipoles 121
3.4.4 Other Asymmetrie Cycloadditions 122
3.5 Asymmetrie Processes Stereocontrolled by Remote Sulfoxides 123
3.5.1 Nucleophilic Processes 123
3.5.1.1 Reactions with Sulfinylated Electrophiles 123
3.5.1.2 Reactions with Sulfinylated Nucleophiles 130
3.6 Asymmetrie Pummerer Reaction 136
References 142
Contents I VII
4 Synthesis and Applications of Chiral Dithioacetal Derivatives 161
Philip C. Bulman Page and Benjamin R. Buckley
4.1 Introduction 161
4.2 Lithiated Dithianes 162
4.3 Alternative Methods 169
4.4 Oxidation Methods for the Construction of Chiral Dithioacetal
Derivatives and Applications in Synthesis 171
4.5 Applications of Chiral Dithioacetal Derivatives in Natural Product
and Biologically Active Compound Synthesis 176
4.6 Summary 177
References 177
5 Synthesis and Use of Chiral Sulfur Ylides 179
Jean-Franqois Briere and Patrick Metzner
5.1 Introduction 179
5.1.1 Reactions of Sulfonium Ylides 179
5.1.2 Methods of Preparation 280
5.1.3 Conditions for Stereocontrol and Theoretical Investigations 182
5.2 Epoxidation Reaction 183
5.2.1 Stoichiometric Use of Sulfides 183
5.2.1.1 Stilbene Oxides 183
5.2.1.2 Unsaturated Epoxides 186
5.2.1.3 Aliphatic Epoxides 186
5.2.1.4 Terminal Epoxides 187
5.2.1.5 Functional Epoxides 187
5.2.2 Catalytic Use of Sulfides 188
5.3 Aziridination 189
5.3.1 Stoichiometric Aziridination, and Mechanism 190
5.3.2 Catalytic Aziridination 192
5.4 Cyclopropanation 194
5.4.1 Stoichiometric Cyclopropanation 195
5.4.2 Catalytic Cyclopropanation 197
5.5 [2,3]-Sigmatropic Rearrangement 199
5.6 Other Reactions 203
5.7 Conclusions 204
References 204
6 Synthesis and Use of Chiral Sulfoximines 209
Christin Worch, Agathe Christine Mayer, and Carsten Bolm
6.1 Introduction 209
6.2 Synthesis and Structural Modification 211
6.3 Applications in Asymmetrie Synthesis 213
6.3.1 Use of Sulfoximines as Chiral Auxiliaries 214
VIIII Contents
6.3.2 Use of Sulfoximines as Chiral Ligands 224
6.4 Condusions 229
References 229
7 Synthesis and Use of Chiral Sulfinamides 233
Chris H. Senanayake, Zhengxu Hart, and Dhileepkumar Krishnamurthy
7.1 Introduction 233
7.2 Synthesis of Chiral Sulfinamides and Chiral Sulfinylimines 234
7.2.1 Background 234
7.2.2 Synthesis of Chiral Sulfinamides 235
7.2.3 Synthesis of Chiral Sulfinylimines 240
7.3 Use of Chiral Sulfinamides 241
7.3.1 Use as Chiral Sulfinyl Auxiliaries 241
7.3.2 Synthesis of Chiral Amines 241
7.3.3 Synthesis of Aziridines 249
7.3.4 Use of Chiral Sulfinamides as Ligands in Catalytic Asymmetrie
Reactions 252
7.3.4.1 Asymmetrie Diels-Alder Reaction 252
7.3.4.2 Asymmetrie Allylic Alkylation Reaction 254
7.3.4.3 Asymmetrie Hydrogenation of Olefins 255
7.3.5 Application of Chiral Sulfinamides in the Synthesis of Biologically
Active Molecules 256
7.3.5.1 Synthesis ofSC-53116 256
7.3.5.2 Total Synthesis of (6R,7S)-7-Amino-7,8-Dihydro-a-Bisabolene 257
7.3.5.3 Asymmetrie Synthesis of (—)-Pateamine 258
7.3.5.4 Synthesis of Polyoxamic Acid Lactone 259
7.3.5.5 Synthesis of Single Enantiomers of Sibutramine and Cetirizine 259
7.4 Summary 261
References 262
8 Asymmetrie Catalysis Using Sulfoxides as Ligands 265
Inmaculada Fernändez and Noureddine Khiar
8.1 Introduction 265
8.2 Some Considerations on the Coordination of Sulfoxides 266
8.3 Sulfoxides as Ligands in Metal-Catalyzed Asymmetrie Catalysis 267
8.3.1 Catalytic Hydrogenations 267
8.3.2 Catalytic Cycloadditions 270
8.3.3 Addition of Diethylzinc to Benzaldehyde 272
8.3.4 Catalytic Allylic Substitutions 273
8.3.5 Utilization of Sulfoxides in Other Metal-Catalyzed Asymmetrie
Processes 279
8.3.5.1 Use of Sulfoxides in Lewis Acid-Lewis Base Bifunctional
Asymmetrie Catalysis 279
Contents I IX
8.3.5.2 Use of Sulfoxides as Chiral Ligands in Combination with Achiral
Catalysts 281
8.3.5.3 Use of Sulfoxides as Ligands in Enantioselective Radical
Allylation 283
8.3.6 Use of Sulfoxides as Neutral Coordinate-Organocatalysts 284
8.4 Condusions 287
References 288
9 Sulfones in Asymmetrie Catalysis 291
Juan Carlos Carretero, Ramön Gömez Arrayäs, and Javier Adrio
9.1 Introduction 291
9.2 Alkenyl Sulfones in Asymmetrie Catalysis 292
9.2.1 Asymmetrie Catalytic Conjugate Addition 292
9.2.2 Asymmetrie Catalytic Conjugate Reduction 297
9.2.3 Asymmetrie Catalytic Radical Addition 298
9.2.4 Asymmetrie Catalytic Cycloadditions 300
9.2.5 Asymmetrie Catalytic Dihydroxylation and Epoxidation Reactions 301
9.3 Ketosulfones 305
9.3.1 Asymmetrie Reduction of Ketosulfones 305
9.3.2 Diels-Alder Reactions 308
9.3.3 Michael-Aldol Reactions 309
9.4 a-Diazo-/?- Ketosulfones 311
9.5 Miscellaneous: Other Substituted Sulfones 314
9.6 Summary 315
References 317
10 Asymmetrie Reaction of a-Sulfenyl Carbanions 321
Shuichi Nakamura and Takeshi Toru
10.1 Asymmetrie Reactions of a-Sulfenyl Carbanions 321
10.1.1 Introduction 321
10.2 Racemization Mechanism and Configurational Stability of a-Sulfenyl
Carbanions 323
10.3 Diastereoselective Reaction of a-Sulfenyl Carbanions 326
10.4 Enantioselective Reaction of a-Sulfenyl Carbanions 329
10.4.1 Reaction Pathway of Enantioselective Reaction of a-Sulfenyl
Carbanions 329
10.4.2 Enantioselective Reactions of a-Sulfenyl Carbanions 332
10.4.3 Enantioselective Reactions of a-Lithiated Dithioacetals 344
10.5 Conclusions 346
References 347
X I Contents
11 Stereoselective Reactions with a-Sulfinyl Carbanions 351
Alessandro Volonterio and Matteo Zanda
11.1 Introduction 351
11.2 Stereochemistry of oc-Sulfinyl Carbanions 352
11.3 Alkylation of a-Sulfinyl Carbanions 354
11.4 Conjugated Additions with a-Sulfinyl Carbanions 357
11.5 Additions of a-Sulfinyl Carbanions to Carbonyl Compounds 360
11.6 Additions of a-Sulfinyl Carbanions to Imines and Related
Compounds 367
11.7 Conclusions 371
References 372
12 Asymmetrie Reactions of or-Sulfonyl Carbanions 375
Hans-Joachim Cais
12.1 Introduction 375
12.2 Configurationally Stable a-Sulfonyl Carbanions 380
12.3 Configurationally Labile a-Sulfonyl Carbanions 382
12.4 Configurationally Labile a-Sulfonyl Carbanions with
an Additional Stereogenic Center 388
References 396
13 Computational Studies on Asymmetrie Reactions with
Sulfur Reagents 399
David Balcells and Feliu Maseras
13.1 Introduction 399
13.2 Directing Effect of Chiral Sulfur Substituents 400
13.3 Sulfur Centers in Chiral Intermediates 403
13.4 Synthesis of Chiral Sulfoxides from Prochiral Sulfides 405
13.5 Synthesis of Chiral Sulfoxides from Racemic Precursors 409
13.6 Other Systems Involving Chiral Sulfur Centers 413
13.7 Conclusions and Perspectives 414
References 435
Index 417 |
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| callnumber-sort | QD 3412 S1 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 7715 |
| classification_tum | CHE 624f CHE 632f |
| ctrlnum | (OCoLC)192081271 (DE-599)DNB987213857 |
| dewey-full | 547.06045 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.06045 |
| dewey-search | 547.06045 |
| dewey-sort | 3547.06045 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| discipline_str_mv | Chemie / Pharmazie Chemie |
| format | Book |
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| id | DE-604.BV023406599 |
| illustrated | Illustrated |
| index_date | 2024-07-02T21:25:48Z |
| indexdate | 2024-07-20T09:45:28Z |
| institution | BVB |
| isbn | 9783527318544 3527318542 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016589281 |
| oclc_num | 192081271 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM |
| owner_facet | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM |
| physical | XVI, 432 S. graph. Darst. |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Organosulfur chemistry in asymmetric synthesis ed. by Takeshi Toru ... Weinheim WILEY-VCH 2008 XVI, 432 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Asymmetric synthesis Enantioselective catalysis Organosulfur compounds Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Schwefelorganische Verbindungen (DE-588)4180419-3 gnd rswk-swf Schwefelorganische Verbindungen (DE-588)4180419-3 s Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Toru, Takeshi Sonstige oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3060774&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016589281&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Organosulfur chemistry in asymmetric synthesis Asymmetric synthesis Enantioselective catalysis Organosulfur compounds Asymmetrische Synthese (DE-588)4135603-2 gnd Schwefelorganische Verbindungen (DE-588)4180419-3 gnd |
| subject_GND | (DE-588)4135603-2 (DE-588)4180419-3 |
| title | Organosulfur chemistry in asymmetric synthesis |
| title_auth | Organosulfur chemistry in asymmetric synthesis |
| title_exact_search | Organosulfur chemistry in asymmetric synthesis |
| title_exact_search_txtP | Organosulfur chemistry in asymmetric synthesis |
| title_full | Organosulfur chemistry in asymmetric synthesis ed. by Takeshi Toru ... |
| title_fullStr | Organosulfur chemistry in asymmetric synthesis ed. by Takeshi Toru ... |
| title_full_unstemmed | Organosulfur chemistry in asymmetric synthesis ed. by Takeshi Toru ... |
| title_short | Organosulfur chemistry in asymmetric synthesis |
| title_sort | organosulfur chemistry in asymmetric synthesis |
| topic | Asymmetric synthesis Enantioselective catalysis Organosulfur compounds Asymmetrische Synthese (DE-588)4135603-2 gnd Schwefelorganische Verbindungen (DE-588)4180419-3 gnd |
| topic_facet | Asymmetric synthesis Enantioselective catalysis Organosulfur compounds Asymmetrische Synthese Schwefelorganische Verbindungen |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3060774&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016589281&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT torutakeshi organosulfurchemistryinasymmetricsynthesis |