Stereoselective Multiple Bond-Forming Transformations in Organic Synthesis

Mitarbeit: Enders, Dieter; Herausgegeben von Rodriguez, Jean; Bonne, Damien

• Gebundenes Buch

Produktbeschreibung

Combining the important research topic of multiple bond-forming transformations with green chemistry, this book helps chemists identify recent sustainable stereoselective synthetic sequences.

- Combines the important research topic of multiple bond-forming transformations with green chemistry and sustainable development
- Offers a valuable resource for preparing compounds with multiple stereogenic centers, an important field for synthetic chemists
- Organizes chapters by molecular structure of final products, making for a handbook-style resource
- Discusses applications of the synthesis of natural products and of drug intermediates
- Brings together otherwise-scattered information about a number of key, efficient chemical reactions

Produktdetails

• Verlag: Wiley & Sons
• 1. Auflage
• Seitenzahl: 480
• Erscheinungstermin: 27. April 2015
• Englisch
• Abmessung: 236mm x 157mm x 30mm
• Gewicht: 10161g
• ISBN-13: 9781118672716
• ISBN-10: 1118672712
• Artikelnr.: 42285437

Autorenporträt

Jean Rodriguez is Professor and Director of the "Institut des Sciences Moléculaires de Marseille" at Aix-Marseille Université, with research interests including the development of new stereoselective domino and multicomponent reactions and their applications. He was awarded the ACROS prize in Organic Chemistry (1998) and the prize of the Division of Organic Chemistry (2009) from the French Chemical Society and was named a Distinguished Senior Member (2013) of the French Chemical Society. Damien Bonne is an assistant professor at Aix-Marseille Université, with research interests including the development of new asymmetric organocatalyzed methodologies and their application in stereoselective synthesis.

Inhaltsangabe

List of Contributors xiii Foreword xvii Preface xix 1 Definitions and
Classifications of MBFTs 1 Damien Bonne and Jean Rodriguez 1.1 Introduction
1 1.2 Definitions 4 1.3 Conclusion and Outlook 6 References 7 PART I
STEREOSELECTIVE SYNTHESIS OF HETEROCYCLES 9 2 Five-Membered Heterocycles 11
Hanmin Huang and Pan Xie 2.1 Introduction 11 2.2 Monocyclic Targets 12
2.2.1 1,3-Dipolar Cycloaddition 12 2.2.2 Michael Addition-Initiated Domino
Process 20 2.2.3 Multicomponent Reactions 23 2.2.4 Carbohalogenation
Reactions 26 2.2.5 Radical Processes 26 2.3 Fused Polycyclic Targets 28
2.3.1 Cycloaddition Reactions 28 2.3.2 Domino Cyclization Reactions 32 2.4
Bridged Polycyclic Targets 34 2.5 Conclusion and Outlook 36 References 37 3
Six-Membered Heterocycles 45 Giammarco Tenti, M. Teresa Ramos, and J.
Carlos Menéndez 3.1 Introduction 45 3.2 Monocyclic Targets 47 3.2.1
Nitrogen-Only Heterocycles 47 3.2.2 Oxygen-Containing Heterocycles 58 3.3
Fused Polycyclic Targets 62 3.3.1 Nitrogen-Only Fused Polycyclic Targets 62
3.3.2 Oxygen-Containing Fused Polycyclic Targets 70 3.3.3 Sulfur-Containing
Fused Polycyclic Targets 74 3.4 Bridged Polycyclic Targets 74 3.4.1 General
Procedure for the Preparation of 2,6-DABCO-Derived Compounds 138 76 3.5
Polycyclic Spiro Targets 77 3.6 Summary and Outlook 79 References 79 4
Other Heterocycles 87 Qian Wang and Jieping Zhu 4.1 Introduction 87 4.2
Synthesis of Medium-Sized Monocyclic, Fused and Bridged Polycyclic
Heterocycles 88 4.2.1 Ring Synthesis by Ring Transformation via
Rearrangements/Ring Expansions 88 4.2.2 Ring Synthesis by Annulation 99 4.3
Summary and Outlook 109 References 109 PART II STEREOSELECTIVE SYNTHESIS OF
CARBOCYCLES 115 5 Three- and Four-Membered Carbocycles 117 Renata Marcia de
Figueiredo, Gilles Niel, and Jean-Marc Campagne 5.1 Introduction 117 5.2
Cyclopropane Derivatives 118 5.2.1 Organocatalysis and Related Reactions
[Michael-Initiated Ring-Closure (MIRC) Reactions] 118 5.2.2 Organometallics
and Metal Catalysis 123 5.2.3 Lewis Acid-Promoted Sequences 133 5.2.4
Pericyclic Domino Strategies 134 5.2.5 Radical Domino Strategies 135 5.3
Cyclobutane Derivatives 136 5.3.1 Organocatalyzed Cyclobutanations 136
5.3.2 Organometallics and Metal Catalysis 137 5.3.3 Acid- or Base-Promoted
Transformations 143 5.3.4 Multicomponent Reactions (MCRs) 145 5.4 Summary
and Outlook 146 References 146 6 Five-Membered Carbocycles 157 Vijay Nair
and Rony Rajan Paul 6.1 Introduction 157 6.2 Monocyclic Targets 158 6.2.1
Metal-Catalyzed Reactions 158 6.2.2 Organocatalytic Reactions 158 6.2.3
Miscellaneous Reactions 167 6.3 Fused Polycyclic Targets 169 6.3.1
Metal-Catalyzed Reactions 169 6.3.2 Organocatalytic Reactions 170 6.3.3
Lewis Acid-Catalyzed Reactions 172 6.3.4 Miscellaneous Reactions 173 6.4
Bridged Polycyclic Targets 176 6.5 Conclusion and Outlook 178 References
179 7 Stereoselective Synthesis of Six-Membered Carbocycles 185 Muriel
Amatore, Corinne Aubert, Marion Barbazanges, Marine Desage-El Murr, and
Cyril Ollivier 7.1 Introduction 185 7.2 Metal-Catalyzed Stereoselective
Multiple Bond-Forming Transformations 186 7.2.1 Introduction 186 7.2.2
Cycloadditions 186 7.2.3 Metal-Catalyzed Cascades as Formal [2+2+2]
Cycloadditions 191 7.2.4 Metal-Catalyzed Cycloisomerization Cascades 192
7.3 Enantioselective Organocatalyzed Synthesis of Six-Membered Rings 195
7.3.1 Organocatalyzed Miscellaneous Reactions 195 7.3.2 Organocatalyzed
Cascade and Multicomponent Reactions 197 7.3.3 Polycyclization Cascade
Reactions 201 7.4 Stereoselective Multiple Bond-Forming Radical
Transformations 202 7.4.1 Intermolecular Cascade Reactions 202 7.4.2
Intramolecular Cascade Reactions 203 7.5 Conclusions 204 References 205 8
Seven- and Eight-Membered Carbocycles 211 Gérard Buono, Hervé Clavier,
Laurent Giordano, and Alphonse Tenaglia 8.1 Introduction 211 8.2
Cycloheptenes 212 8.3 Cycloheptadienes 219 8.4 Cycloheptatrienes 221 8.5
Cyclooctenes 222 8.6 Cyclooctadienes 225 8.7 Cyclooctatrienes 229 8.8
Cyclooctatetraenes 234 8.9 Concluding Remarks 235 References 235 PARTIII
STEREOSELECTIVE SYNTHESIS OF SPIROCYCLIC COMPOUNDS 241 9 Metal-Assisted
Methodologies 243 Gaëlle Chouraqui, Laurent Commeiras, and Jean-Luc Parrain
9.1 Introduction 243 9.2 Quaternary Spirocenter 244 9.2.1 Copper-Assisted
Methodologies 245 9.2.2 Gold-Assisted Methodologies 247 9.2.3
Palladium-Assisted Methodologies 247 9.2.4 Rhodium-Assisted Methodologies
251 9.2.5 Platinum-Assisted Methodologies 252 9.3
alpha-Heteroatom-Substituted Spirocenter 252 9.3.1 Zinc-, Magnesium-, and
Copper-Assisted Methodologies 253 9.3.2 Titanium-Assisted Methodologies 254
9.3.3 Gold- and Platinum-Assisted Methodologies 255 9.3.4
Palladium-Assisted Methodologies 258 9.3.5 Rhodium-Assisted Methodologies
259 9.4 alpha,alpha'-Diheteroatom-Substituted Spirocenter 261 9.5
Conclusion and Outlook 264 References 265 10 Organocatalyzed Methodologies
271 Ramon Rios 10.1 Introduction 271 10.2 Enantioselective Synthesis of
All-Carbon Spirocenters 275 10.2.1 Organocatalytic Enantioselective
Methodologies for the Synthesis of Spirooxindoles 275 10.2.2 Other
Spirocycles 292 10.3 Enantioselective Synthesis Spirocenters with at Least
One Heteroatom 299 10.3.1 Synthesis of Spirooxindoles 299 10.3.2 Synthesis
of Other Spirocycles 301 10.4 Conclusion and Outlook 301 References 302
PARTIV STEREOSELECTIVE SYNTHESIS OF ACYCLIC COMPOUNDS 307 11
Metal-Catalyzed Methodologies 309 Gabriela Guillena and Diego J. Ramón 11.1
Introduction 309 11.2 Anion Relay Approach 310 11.3 Mannich Reaction 312
11.3.1 Diastereoselective Approach 312 11.3.2 Enantioselective Approach 312
11.4 Reactions Involving Isonitriles 314 11.4.1 Diastereoselective
Passerini Reaction 314 11.4.2 Enantioselective Passerini Reaction 315
11.4.3 Diastereoselective Ugi Reaction 316 11.5 1,2-Addition-Type Processes
317 11.5.1 Diastereoselective Approach 317 11.5.2 Enantioselective Approach
320 11.6 Michael-Type Processes 324 11.6.1 Diastereoselective Approach 324
11.6.2 Enantioselective Approach 327 11.7 Summary and Outlook 331
References 332 12 Organocatalyzed Methodologies 339 Vincent Coeffard,
Christine Greck, Xavier Moreau, and Christine Thomassigny 12.1 Introduction
339 12.2 Aminocatalysis 340 12.2.1 Enamine-Enamine Activation 340 12.2.2
Iminium-Enamine Activation 343 12.3 N-Heterocyclic Carbene (NHC) Activation
353 12.4 H-Bonding Activation 357 12.5 Phase-Transfer Catalysis 358 12.6
Summary and Outlook 359 References 359 PART V MULTIPLE BOND-FORMING
TRANSFORMATIONS: SYNTHETIC APPLICATIONS 363 13 MBFTs for the Total
Synthesis of Natural Products 365 Yanxing Jia 13.1 Introduction 365 13.2
Anionic-Initiated MBFTs 366 13.3 Cationic-Initiated MBFTs 371 13.4
Radical-Mediated MBFTs 375 13.5 Pericyclic MBFTs 379 13.6
Transition-Metal-Catalyzed MBFTs 385 13.7 Summary and Outlook 388
References 390 14 Synthesis of Biologically Relevant Molecules 393 Matthijs
J. van Lint, Eelco Ruijter, and Romano V.A. Orru 14.1 Introduction 393 14.2
Organocatalyzed MBFTs for BRMs 394 14.3 Multicomponent MBFTs for BRMs 404
14.4 Palladium-Catalyzed MBFTs for BRMs 413 14.5 Conclusion and Outlook 418
References 419 15 Industrial Applications of Multiple Bond-Forming
Transformations (MBFTs) 423 Tryfon Zarganes-Tzitzikas, Ahmad Yazbak,
Alexander Dömling 15.1 Introduction 423 15.2 Applications of MBFTs 424
15.2.1 Xylocaine 424 15.2.2 Almorexant 424 15.2.3 (.)-Oseltamivir
(Tamiflu(r)) 427 15.2.4 Telaprevir (Incivek(r)) 429 15.2.5 Ezetimibe
(Zetia(r)) 431 15.2.6 Crixivan (Indinavir(r)) 433 15.2.7 Oxytocine
Antagonists: Retosiban and Epelsiban 436 15.2.8 Praziquantel
(Biltricide(r)) 439 15.3 Summary and Outlook 442 References 442 Index 447