Molecular Rearrangements in Organic Synthesis by Christian M. Rojas (informative)
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Authors of: Molecular Rearrangements in Organic Synthesis by Christian M. Rojas
Christian M. Rojas
Table of Contents in Molecular Rearrangements in Organic Synthesis by Christian M. Rojas
Cover
LIST OF CONTRIBUTORS
PREFACE
PART I: 1,2-MIGRATIONS
CHAPTER 1: PINACOLAND SEMIPINACOLREARRANGEMENTS IN TOTAL
SYNTHESIS
1.1 INTRODUCTION
1.2 PINACOLREACTION
1.3 SEMIPINACOLREARRANGEMENT
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 α-DIAZOCARBONYLCOMPOUNDS
3.5 RECENT SYNTHETIC APPLICATIONS OF THE WOLFF
REARRANGEMENT
3.6 CONCLUSION AND OUTLOOK
REFERENCES
CHAPTER 4: ALKYLAND ACYLAZIDE REARRANGEMENTS
4.1 INTRODUCTION
4.2 ALKYLAZIDE REARRANGEMENTS
4.3 ACYLAZIDE 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 HISTORICALPERSPECTIVE
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 FUNCTIONALGROUPS
5.7 SUMMARY AND OUTLOOK
REFERENCES
CHAPTER 6: BROOK REARRANGEMENT
6.1 INTRODUCTION
6.2 MECHANISM2a,b
6.3 METHODS FOR GENERATION OF α-SILYLALKOXIDES
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 α-SILYLALCOHOLS
6.6 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS
TRIGGERED BY ADDITION OF SILYLMETALLIC REAGENTS
6.7 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS IN α-
SILYLALKOXIDES GENERATED VIA REGIOSELECTIVE β-RING-OPENING
OF α,β-EPOXYSILANES BY A NUCLEOPHILE
6.8 SYNTHETIC REACTIONS USING BROOK REARRANGEMENTS IN α-
SILYLALKOXIDES GENERATED BY A BASE-INDUCED RING OPENING OF
α,β-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-Π-METHANE AND RELATED
REARRANGEMENT REACTIONS IN CHEMICALSYNTHESIS
9.1 INTRODUCTION: THE BASIC PROCESS AND ITS VARIANTS
9.2 MECHANISTIC FEATURES AND COMPETING REACTIONS
9.3 STRUCTURALREQUIREMENTS 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 THERMALVCP–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 PHOTOCHEMICALVCP–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 GENERALDISCUSSION 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
NATURALPRODUCT 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 ALLYLPROPARGYLETHERS
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–STILLREARRANGEMENT
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 CONFIGURATIONALLABILITY 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 VINYLANION SYNTHONS ACCESSIBLE VIA MISLOW–EVANS
REARRANGEMENT
18.11 SEQUENTIALPROCESSES INCORPORATING THE MISLOW–EVANS
REARRANGEMENT
18.12 HETEROATOM [2,3]-REARRANGEMENT VARIANTS
18.13 [2,3]-REARRANGEMENTS OF PROPARGYLAND 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 POWERFULTOOLS IN
ORGANIC SYNTHESIS
20.1 INTRODUCTION
20.2 CLASSICALPUMMERER 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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