Molecular Rearrangements in Organic Synthesis

Name: Molecular Rearrangements in Organic Synthesis
Brand: Wiley
Price: 171.99 EUR
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Christian M. Rojas(Autor*in)

Wiley (Verlag)

Erschienen am 1. Oktober 2015

528 Seiten

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978-1-118-93989-5 (ISBN)

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Inhalt

Intro
Title Page
Copyright
Table of Contents
LIST OF CONTRIBUTORS
PREFACE
PART I: 1,2-MIGRATIONS
CHAPTER 1: PINACOL AND SEMIPINACOL REARRANGEMENTS IN TOTAL SYNTHESIS
1.1 INTRODUCTION
1.2 PINACOL REACTION
1.3 SEMIPINACOL REARRANGEMENT
1.4 CONCLUSION
REFERENCES
CHAPTER 2: BAEYER-VILLIGER (BV) OXIDATION/REARRANGEMENT IN ORGANIC SYNTHESIS
2.1 INTRODUCTION
2.2 MECHANISM
2.3 SYNTHETIC APPLICATIONS
2.4 SUMMARY AND OUTLOOK
REFERENCES
CHAPTER 3: THE WOLFF REARRANGEMENT: TACTICS, STRATEGIES AND RECENT APPLICATIONS IN ORGANIC SYNTHESIS
3.1 INTRODUCTION
3.2 TACTICS AND STRATEGIES VIA THE WOLFF REARRANGEMENT
3.3 MECHANISTIC FEATURES AND SELECTIVITY ISSUES OF THE WOLFF REARRANGEMENT
3.4 PREPARATION OF a-DIAZOCARBONYL COMPOUNDS
3.5 RECENT SYNTHETIC APPLICATIONS OF THE WOLFF REARRANGEMENT
3.6 CONCLUSION AND OUTLOOK
REFERENCES
CHAPTER 4: ALKYL AND ACYL AZIDE REARRANGEMENTS
4.1 INTRODUCTION
4.2 ALKYL AZIDE REARRANGEMENTS
4.3 ACYL AZIDE REARRANGEMENTS
4.4 HOFMANN REARRANGEMENT
4.5 LOSSEN REARRANGEMENT
4.6 CONCLUSION
REFERENCES
CHAPTER 5: BECKMANN REARRANGEMENTS AND FRAGMENTATIONS IN ORGANIC SYNTHESIS
5.1 INTRODUCTION
5.2 STRATEGIC PLANNING: A HISTORICAL PERSPECTIVE
5.3 RECENT APPLICATIONS TOWARD THE SYNTHESIS OF NATURAL PRODUCTS
5.4 ACCESS TO DIVERSE SCAFFOLDS VIA THE BECKMANN REACTION
5.5 FORMATION OF HETEROCYCLIC SCAFFOLDS
5.6 SYNTHESIS OF FUNCTIONAL GROUPS
5.7 SUMMARY AND OUTLOOK
REFERENCES
CHAPTER 6: BROOK REARRANGEMENT
6.1 INTRODUCTION
6.2 MECHANISM2a,b
6.3 METHODS FOR GENERATION OF a-SILYL ALKOXIDES
6.4 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS IN THE REACTIONS OF ACYLSILANES WITH NUCLEOPHILES
6.5 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS TRIGGERED BY DEPROTONATION OF a-SILYL ALCOHOLS
6.6 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS TRIGGERED BY ADDITION OF SILYLMETALLIC REAGENTS
6.7 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS IN a-SILYL ALKOXIDES GENERATED VIA REGIOSELECTIVE ß-RING-OPENING OF a,ß-EPOXYSILANES BY A NUCLEOPHILE
6.8 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS IN a-SILYL ALKOXIDES GENERATED BY A BASE-INDUCED RING OPENING OF a,ß-EPOXYSILANES
6.9 CONCLUSION
REFERENCES
PART II: 1,2-MIGRATIONS VIA THREE-MEMBERED RINGS
CHAPTER 7: THE QUASI-FAVORSKII REARRANGEMENT
7.1 Introduction
7.2 RETRONS OF THE QUASI-FAVORSKII REARRANGEMENT
7.3 MECHANISTIC CONSIDERATIONS IN THE QUASI-FAVORSKII REARRANGEMENT
7.4 THE PREPARATION OF SUBSTRATES FOR THE QUASI-FAVORSKII REARRANGEMENT
7.5 APPLICATIONS OF THE QUASI-FAVORSKII REARRANGEMENT IN SYNTHESIS
7.6 CONCLUSIONS AND PROSPECTS
ACKNOWLEDGMENTS
REFERENCES
CHAPTER 8: THE RAMBERG-BÄCKLUND REACTION
8.1 INTRODUCTION
8.2 METHODS TO SYNTHESIZE SULFONES AS RBR PRECURSORS
8.3 VARIATIONS OF THE RBR
8.4 MECHANISTIC EVALUATION OF THE RBR
8.5 STRATEGIC CONSIDERATIONS RELEVANT TO THE USE OF THE RBR IN SYNTHESIS
8.6 UTILITY, SCOPE, AND LIMITATIONS OF THE RBR
8.7 RECENT APPLICATIONS OF THE RBR IN THE SYNTHESIS OF COMPLEX TARGET STRUCTURES
8.8 CONCLUDING REMARKS
ACKNOWLEDGMENTS
REFERENCES
CHAPTER 9: APPLICATIONS OF DI-?-METHANE AND RELATED REARRANGEMENT REACTIONS IN CHEMICAL SYNTHESIS
9.1 INTRODUCTION: THE BASIC PROCESS AND ITS VARIANTS
9.2 MECHANISTIC FEATURES AND COMPETING REACTIONS
9.3 STRUCTURAL REQUIREMENTS OF SUBSTRATES AND MATTERS OF REGIO- AND STEREO-CHEMISTRY
9.4 SYNTHETIC ROUTES TO SUBSTRATES AND APPLICATIONS IN SYNTHESIS
9.5 OUTLOOK
REFERENCES
PART III: 1,3-TRANSPOSITIONS
CHAPTER 10: PAYNE REARRANGEMENT
10.1 BACKGROUND ON THE PAYNE REARRANGEMENT
10.2 SYNTHETIC APPLICATIONS OF 2,3-EPOXY ALCOHOLS
10.3 UTILIZATION OF THE PAYNE REARRANGEMENT FOR THE PREPARATION OF FLUORINE-CONTAINING COMPOUNDS
10.4 CONCLUSION
REFERENCES
CHAPTER 11: VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT
11.1 INTRODUCTION
11.2 THERMAL VCP-CP REARRANGEMENT
11.3 ACID-MEDIATED VCP-CP REARRANGEMENT
11.4 MECHANISMS
11.5 HETEROATOM-CONTAINING ANALOGUES OF THE VCP-CP REARRANGEMENT
11.6 APPLICATIONS IN SYNTHESIS
11.7 PHOTOCHEMICAL VCP-CP REARRANGEMENT
11.8 METAL-CATALYZED VCP-CP REARRANGEMENT
11.9 HETEROATOM VARIANTS OF THE METAL-CATALYZED VCP-CP REARRANGEMENT
11.10 SUMMARY AND OUTLOOK
REFERENCES
CHAPTER 12: FERRIER CARBOCYCLIZATION REACTION
12.1 INTRODUCTION
12.2 GENERAL DISCUSSION AND MECHANISTIC FEATURES
12.3 SYNTHETIC STRATEGIES BASED ON THE FERRIER CARBOCYCLIZATION REACTION
12.4 METHODOLOGIES FOR ASSEMBLING THE FERRIER CARBOCYCLIZATION REACTION SUBSTRATES
12.5 APPLICATIONS OF THE FERRIER CARBOCYCLIZATION REACTION IN NATURAL PRODUCT SYNTHESIS
12.6 CONCLUSION
REFERENCES
Part IV: [3,3]- AND [2,3]-SIGMATROPIC REARRANGEMENTS
CHAPTER 13: THE CLAISEN REARRANGEMENT
13.1 INTRODUCTION
13.2 STRATEGIC PLANNING FOR THE CLAISEN REARRANGEMENT REACTION
13.3 MECHANISTIC FEATURES OF THE CLAISEN REARRANGEMENT REACTION
13.4 METHODOLOGIES FOR SYNTHESIS OF CLAISEN REARRANGEMENT SUBSTRATES
13.5 APPLICATIONS OF THE CLAISEN REARRANGEMENT REACTION IN TARGET-ORIENTED SYNTHESIS
13.6 CONCLUSIONS
REFERENCES
CHAPTER 14: [3,3]-SIGMATROPIC REARRANGEMENTS WITH HETEROATOM-HETEROATOM BONDS
14.1 INTRODUCTION
14.2 [3,3]-SIGMATROPIC REARRANGEMENTS OF N-O BONDS
14.3 [3,3]-SIGMATROPIC REARRANGEMENTS OF N-N BONDS
14.4 [3,3]-REARRANGEMENTS OF N-N BOND FRAGMENTS THAT ELIMINATE N2
14.5 SUMMARY
REFERENCES
CHAPTER 15: [2,3]-REARRANGEMENTS OF AMMONIUM ZWITTERIONS
15.1 INTRODUCTION
15.2 [2,3]-MEISENHEIMER REARRANGEMENT OF AMINE N-OXIDES
15.3 [2,3]-STEVENS REARRANGEMENT OF AMMONIUM YLIDES
15.4 CONCLUSION AND OUTLOOK
REFERENCES
CHAPTER 16: OXONIUM YLIDE REARRANGEMENTS IN SYNTHESIS
16.1 INTRODUCTION
16.2 Applications in Synthesis: Oxonium Ylide [2,3]-Sigmatropic Rearrangements
16.3 Applications in Synthesis: Oxonium Ylide [1,2]-Stevens Rearrangements
16.4 CONCLUDING REMARKS
REFERENCES
CHAPTER 17: THE [2,3]-WITTIG REARRANGEMENT
17.1 INTRODUCTION
17.2 [2,3]-WITTIG REARRANGEMENT OF ALLYL PROPARGYL ETHERS
17.3 FACTORS DETERMINING [2,3]-WITTIG VERSUS [1,2]-WITTIG REARRANGEMENT
17.4 ACYCLIC [2,3]-WITTIG REARRANGEMENT OF PROPARGYL-ALLYL ETHERS
17.5 [2,3]-WITTIG-STILL REARRANGEMENT
17.6 ASYMMETRIC [2,3]-WITTIG REARRANGEMENT
17.7 AZA-[2,3]-WITTIG REARRANGEMENT
17.8 OTHER WITTIG REARRANGEMENTS AND MISCELLANEOUS
17.9 CONCLUSION
REFERENCES
CHAPTER 18: THE MISLOW-EVANS REARRANGEMENT
18.1 INTRODUCTION
PART 1. MECHANISTIC ASPECTS AND THE [2,3] NATURE OF THE REARRANGEMENT
18.2 CONFIGURATIONAL LABILITY OF ALLYLIC SULFOXIDES
18.3 DEUTERIUM LABELING TO TRACK [2,3] PATHWAY
18.4 TRANSITION STATE FEATURES
18.5 EQUILIBRIUM BETWEEN SULFOXIDE AND SULFENATE
18.6 CHIRALITY TRANSFER
PART 2. SYNTHETIC CONSIDERATIONS AND APPLICATIONS
18.7 ALKENE STEREOSELECTIVITY
18.8 DIASTEREOFACE SELECTIVITY IN THE REARRANGEMENT
18.9 EPIMERIZATIONS VIA MISLOW-EVANS REARRANGEMENT SEQUENCES
18.10 VINYL ANION SYNTHONS ACCESSIBLE VIA MISLOW-EVANS REARRANGEMENT
18.11 SEQUENTIAL PROCESSES INCORPORATING THE MISLOW-EVANS REARRANGEMENT
18.12 HETEROATOM [2,3]-REARRANGEMENT VARIANTS
18.13 [2,3]-REARRANGEMENTS OF PROPARGYL AND ALLENYL SULFENATES AND SULFOXIDES
18.14 CONCLUSION
REFERENCES
PART V: IPSO REARRANGEMENTS
CHAPTER 19: SMILES REARRANGEMENTS
19.1 INTRODUCTION
19.2 SCOPE AND MECHANISTIC FEATURES
19.3 APPLICATION OF SMILES REARRANGEMENTS
19.4 CONCLUSION
REFERENCES
CHAPTER 20: PUMMERER-TYPE REACTIONS AS POWERFUL TOOLS IN ORGANIC SYNTHESIS
20.1 INTRODUCTION
20.2 CLASSICAL PUMMERER REACTION
20.3 VINYLOGOUS PUMMERER REACTION
20.4 INTERRUPTED AND ADDITIVE PUMMERER REACTIONS
20.5 CONNECTIVE PUMMERER REACTION
20.6 PUMMERER REARRANGEMENT IN MULTIPLE-REACTION PROCESSES
20.7 OTHER PUMMERER REARRANGEMENTS
20.8 SUMMARY AND OUTLOOK
REFERENCES
INDEX
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