
Stereoselective Multiple Bond-Forming Transformations in Organic Synthesis.
Title:
Stereoselective Multiple Bond-Forming Transformations in Organic Synthesis.
Author:
Rodriguez, Jean.
ISBN:
9781119006329
Personal Author:
Edition:
1st ed.
Physical Description:
1 online resource (472 pages)
Contents:
Cover -- Title Page -- Copyright -- Contents -- List of Contributors -- Foreword -- Preface -- Chapter 1 Definitions and Classifications of MBFTs -- 1.1 Introduction -- 1.2 Definitions -- 1.3 Conclusion and Outlook -- References -- Part I Stereoselective Synthesis of Heterocycles -- Chapter 2 Five-Membered Heterocycles -- 2.1 Introduction -- 2.2 Monocyclic Targets -- 2.2.1 1,3-Dipolar Cycloaddition -- 2.2.2 Michael Addition-Initiated Domino Process -- 2.2.3 Multicomponent Reactions -- 2.2.4 Carbohalogenation Reactions -- 2.2.5 Radical Processes -- 2.3 Fused Polycyclic Targets -- 2.3.1 Cycloaddition Reactions -- 2.3.2 Domino Cyclization Reactions -- 2.4 Bridged Polycyclic Targets -- 2.5 Conclusion and Outlook -- References -- Chapter 3 Six-Membered Heterocycles -- 3.1 Introduction -- 3.2 Monocyclic Targets -- 3.2.1 Nitrogen-Only Heterocycles -- 3.2.2 Oxygen-Containing Heterocycles -- 3.3 Fused Polycyclic Targets -- 3.3.1 Nitrogen-Only Fused Polycyclic Targets -- 3.3.2 Oxygen-Containing Fused Polycyclic Targets -- 3.3.3 Sulfur-Containing Fused Polycyclic Targets -- 3.4 Bridged Polycyclic Targets -- 3.4.1 General Procedure for the Preparation of 2,6-DABCO-Derived Compounds 138 -- 3.5 Polycyclic Spiro Targets -- 3.6 Summary and Outlook -- References -- Chapter 4 Other Heterocycles -- 4.1 Introduction -- 4.2 Synthesis of Medium-Sized Monocyclic, Fused and Bridged Polycyclic Heterocycles -- 4.2.1 Ring Synthesis by Ring Transformation via Rearrangements/Ring Expansions -- 4.2.2 Ring Synthesis by Annulation -- 4.3 Summary and Outlook -- References -- Part II Stereoselective Synthesis of Carbocycles -- Chapter 5 Three- and Four-Membered Carbocycles -- 5.1 Introduction -- 5.2 Cyclopropane Derivatives.
5.2.1 Organocatalysis and Related Reactions [Michael-Initiated Ring-Closure (MIRC) Reactions] -- 5.2.2 Organometallics and Metal Catalysis -- 5.2.3 Lewis Acid-Promoted Sequences -- 5.2.4 Pericyclic Domino Strategies -- 5.2.5 Radical Domino Strategies -- 5.3 Cyclobutane Derivatives -- 5.3.1 Organocatalyzed Cyclobutanations -- 5.3.2 Organometallics and Metal Catalysis -- 5.3.3 Acid- or Base-Promoted Transformations -- 5.3.4 Multicomponent Reactions (MCRs) -- 5.4 Summary and Outlook -- References -- Chapter 6 Five-Membered Carbocycles -- 6.1 Introduction -- 6.2 Monocyclic Targets -- 6.2.1 Metal-Catalyzed Reactions -- 6.2.2 Organocatalytic Reactions -- 6.2.3 Miscellaneous Reactions -- 6.3 Fused Polycyclic Targets -- 6.3.1 Metal-Catalyzed Reactions -- 6.3.2 Organocatalytic Reactions -- 6.3.3 Lewis Acid-Catalyzed Reactions -- 6.3.4 Miscellaneous Reactions -- 6.4 Bridged Polycyclic Targets -- 6.5 Conclusion and Outlook -- References -- Chapter 7 Stereoselective Synthesis of Six-Membered Carbocycles -- 7.1 Introduction -- 7.2 Metal-Catalyzed Stereoselective Multiple Bond-Forming Transformations -- 7.2.1 Introduction -- 7.2.2 Cycloadditions -- 7.2.3 Metal-Catalyzed Cascades as Formal [2+2+2] Cycloadditions -- 7.2.4 Metal-Catalyzed Cycloisomerization Cascades -- 7.3 Enantioselective Organocatalyzed Synthesis of Six-Membered Rings -- 7.3.1 Organocatalyzed Miscellaneous Reactions -- 7.3.2 Organocatalyzed Cascade and Multicomponent Reactions -- 7.3.3 Polycyclization Cascade Reactions -- 7.4 Stereoselective Multiple Bond-Forming Radical Transformations -- 7.4.1 Intermolecular Cascade Reactions -- 7.4.2 Intramolecular Cascade Reactions -- 7.5 Conclusions -- References -- Chapter 8 Seven- and Eight-Membered Carbocycles -- 8.1 Introduction -- 8.2 Cycloheptenes -- 8.3 Cycloheptadienes -- 8.4 Cycloheptatrienes -- 8.5 Cyclooctenes.
8.6 Cyclooctadienes -- 8.7 Cyclooctatrienes -- 8.8 Cyclooctatetraenes -- 8.9 Concluding Remarks -- References -- Part III Stereoselective Synthesis of Spirocyclic Compounds -- Chapter 9 Metal-Assisted Methodologies -- 9.1 Introduction -- 9.2 Quaternary Spirocenter -- 9.2.1 Copper-Assisted Methodologies -- 9.2.2 Gold-Assisted Methodologies -- 9.2.3 Palladium-Assisted Methodologies -- 9.2.4 Rhodium-Assisted Methodologies -- 9.2.5 Platinum-Assisted Methodologies -- 9.3 α-Heteroatom-Substituted Spirocenter -- 9.3.1 Zinc-, Magnesium-, and Copper-Assisted Methodologies -- 9.3.2 Titanium-Assisted Methodologies -- 9.3.3 Gold- and Platinum-Assisted Methodologies -- 9.3.4 Palladium-Assisted Methodologies -- 9.3.5 Rhodium-Assisted Methodologies -- 9.4 α,α'-Diheteroatom-Substituted Spirocenter -- 9.5 Conclusion and Outlook -- References -- Chapter 10 Organocatalyzed Methodologies -- 10.1 Introduction -- 10.2 Enantioselective Synthesis of All-Carbon Spirocenters -- 10.2.1 Organocatalytic Enantioselective Methodologies for the Synthesis of Spirooxindoles -- 10.2.2 Other Spirocycles -- 10.3 Enantioselective Synthesis Spirocenters with at Least One Heteroatom -- 10.3.1 Synthesis of Spirooxindoles -- 10.3.2 Synthesis of Other Spirocycles -- 10.4 Conclusion and Outlook -- References -- Part IV Stereoselective Synthesis of Acyclic Compounds -- Chapter 11 Metal-Catalyzed Methodologies -- 11.1 Introduction -- 11.2 Anion Relay Approach -- 11.3 Mannich Reaction -- 11.3.1 Diastereoselective Approach -- 11.3.2 Enantioselective Approach -- 11.4 Reactions Involving Isonitriles -- 11.4.1 Diastereoselective Passerini Reaction -- 11.4.2 Enantioselective Passerini Reaction -- 11.4.3 Diastereoselective Ugi Reaction -- 11.5 1,2-Addition-Type Processes -- 11.5.1 Diastereoselective Approach -- 11.5.2 Enantioselective Approach.
11.6 Michael-Type Processes -- 11.6.1 Diastereoselective Approach -- 11.6.2 Enantioselective Approach -- 11.7 Summary and Outlook -- References -- Chapter 12 Organocatalyzed Methodologies -- 12.1 Introduction -- 12.2 Aminocatalysis -- 12.2.1 Enamine-Enamine Activation -- 12.2.2 Iminium-Enamine Activation -- 12.3 N-Heterocyclic Carbene (NHC) Activation -- 12.4 H-Bonding Activation -- 12.5 Phase-Transfer Catalysis -- 12.6 Summary and Outlook -- References -- Part V Multiple Bond-Forming Transformations: Synthetic Applications -- Chapter 13 MBFTs for the Total Synthesis of Natural Products -- 13.1 Introduction -- 13.2 Anionic-Initiated MBFTs -- 13.3 Cationic-Initiated MBFTs -- 13.4 Radical-Mediated MBFTs -- 13.5 Pericyclic MBFTs -- 13.6 Transition-Metal-Catalyzed MBFTs -- 13.7 Summary and Outlook -- References -- Chapter 14 Synthesis of Biologically Relevant Molecules -- 14.1 Introduction -- 14.2 Organocatalyzed MBFTs for BRMs -- 14.3 Multicomponent MBFTs for BRMs -- 14.4 Palladium-Catalyzed MBFTs for BRMs -- 14.5 Conclusion and Outlook -- References -- Chapter 15 Industrial Applications of Multiple Bond-Forming Transformations (MBFTs) -- 15.1 Introduction -- 15.2 Applications of MBFTs -- 15.2.1 Xylocaine -- 15.2.2 Almorexant -- 15.2.3 (-)-Oseltamivir (Tamiflu®) -- 15.2.4 Telaprevir (Incivek®) -- 15.2.5 Ezetimibe (Zetia®) -- 15.2.6 Crixivan (Indinavir®) -- 15.2.7 Oxytocine Antagonists: Retosiban and Epelsiban -- 15.2.8 Praziquantel (Biltricide®) -- 15.3 Summary and Outlook -- References -- Index -- EULA.
Abstract:
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.
Local Note:
Electronic reproduction. Ann Arbor, Michigan : ProQuest Ebook Central, 2017. Available via World Wide Web. Access may be limited to ProQuest Ebook Central affiliated libraries.
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