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Comprehensive Organic Synthesis
2nd Edition - February 14, 2014
Editors: Paul Knochel, Gary A Molander
Language: English
Hardback ISBN:9780080977423
9 7 8 - 0 - 0 8 - 0 9 7 7 4 2 - 3
eBook ISBN:9780080977430
9 7 8 - 0 - 0 8 - 0 9 7 7 4 3 - 0
The second edition of Comprehensive Organic Synthesis—winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers—builds upon the…Read more
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The second edition of Comprehensive Organic Synthesis—winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers—builds upon the highly respected first edition in drawing together the new common themes that underlie the many disparate areas of organic chemistry. These themes support effective and efficient synthetic strategies, thus providing a comprehensive overview of this important discipline.
Fully revised and updated, this new set forms an essential reference work for all those seeking information on the solution of synthetic problems, whether they are experienced practitioners or chemists whose major interests lie outside organic synthesis. In addition, synthetic chemists requiring the essential facts in new areas, as well as students completely new to the field, will find Comprehensive Organic Synthesis, Second Edition, Nine Volume Set an invaluable source, providing an authoritative overview of core concepts.
Winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers
Contains more than170 articles across nine volumes, including detailed analysis of core topics such as bonds, oxidation, and reduction
Includes more than10,000 schemes and images
Fully revised and updated; important growth areas—including combinatorial chemistry, new technological, industrial, and green chemistry developments—are covered extensively
University and research libraries, especially with collections in organic or heterocyclic chemistry; corporations engaged in industrial chemistry or organic synthesis and government agencies regulating these areas.
Editors-in-Chief
Volume Editors
Preface
Permission Acknowledgments
Volume 1: Additions to C–X Π-Bonds, Part 1
Introduction to Volume 1: Additions to CX π-Bonds, Part 1
1.01 Carbanions of Alkali and Alkaline-Earth Cations: (II) Selectivity of Carbonyl Addition Reactions
Abstract
Glossary
1.01.1 Introduction
1.01.2 Additions of Achiral Reagents to Chiral Substrates
1.01.3 Additions of Chiral Reagents to Achiral Substrates
References
1.02 Organosilicon Reagents: Vinyl-, Alkynyl-, and Arylsilanes
Abstract
Glossary
1.02.1 Introduction
1.02.2 Characteristics of Organosilicon Compounds
1.02.3 Vinylsilanes
1.02.4 Alkynylsilanes
1.02.5 Arylsilanes
References
1.03 Organoaluminum Reagents
Abstract
Glossary
1.03.1 Introduction from the View Point on the Preparation of Organoaluminum Reagents
1.03.2 Uncatalyzed 1,2-Addition of Organoaluminum Reagents
1.03.3 Enantioselective 1,2-Addition of Organoaluminum Reagents to Carbonyl Compounds Catalyzed by Chiral Metal Complex
1.03.4 Rational Design of Organoaluminum Lewis Acid for Selective 1,2-Addition
References
1.04 Regio-, Diastereo-, and Enantioselective Addition of Organocopper Reagents onto CO and CN Bonds
Abstract
Glossary
1.04.1 Introduction
1.04.2 1,2-Additions to Aldehydes and Ketones
1.04.3 1,2 Addition to Imines and Derivatives
1.04.4 Catalytic and Asymmetric Copper-Mediated Reactions
1.04.5 Miscellaneous
1.04.6 Conclusion
References
1.05 Organotitanium and Organozirconium Reagents
Abstract
Glossary
1.05.1 Introduction
1.05.2 Preparation of Principal Organotitanium and Organozirconium Reagents
1.05.3 Carbonyl Addition Reactions
References
1.06 Organochromium Reagents
Abstract
1.06.1 Introduction
1.06.2 C–C Single Bond Formation
1.06.3 C–C Double Bond Formation
1.06.4 Miscellaneous Carbon–Carbon Bond Formation
1.06.5 Conclusion
References
1.07 Recent Advances in Organozinc Reagents
Abstract
Glossary
1.07.1 Introduction
1.07.2 Addition of Organozinc Reagents
1.07.3 Addition of Reformatsky Reagents
1.07.4 Applications of Dialkylzincs as Radical Reagents
References
1.08 Organocerium Reagents
Glossary
1.08.1 Introduction
1.08.2 Organocerium Reagents
1.08.3 Cerium Enolates
1.08.4 Application in Organic Synthesis
References
1.09 Samarium and Ytterbium Reagents
Abstract
Glossary
1.09.1 Introduction and Scope
1.09.2 Zero Valent Yb and Sm
1.09.3 Divalent Sm and Yb
1.09.4 Trivalent Sm and Yb
References
1.10 Lewis Acid Promoted Addition Reactions of Organometallic Compounds
Abstract
1.10.1 Introduction
1.10.2 LAs Addition to Aldehydes and Ketones
1.10.3 LAs in Additions to Acid Derivatives
1.10.4 LAs in Additions to Imines and Related Derivatives
References
1.11 Nucleophilic Addition of Nonstabilized Carbanions to Imines and Imine Derivatives
Abstract
Glossary
1.11.1 Introduction
1.11.2 1,2-Additions of Unstabilized Carbanions to Imines and Imine Derivatives
1.11.3 Summary and Outlook
References
1.12 Sulfur and Selenium Stabilization
Abstract
Glossary
1.12.1 Introduction
1.12.2 Sulfenyl-Stabilized Carbanions
1.12.3 Sulfinyl-Stabilized Carbanions
1.12.4 Sulfonyl-Stabilized Carbanions
1.12.5 Sulfonimidoyl-Stabilized Carbanions
1.12.6 Selenium-Stabilized Carbanions
References
1.13 Benzoin and Aza-benzoin
Abstract
Glossary
1.13.1 Introduction
1.13.2 Benzoin and Aza-Benzoin Condensations with Stoichiometric Acyl Anion Equivalents
2.11.5 Promiscuous Enzyme Function – Hydroxynitrile Lyase-Catalyzed Nitroaldol Reaction
2.11.6 Conclusion
Acknowledgments
References
2.12 Zinc Enolates: The Reformatsky and Blaise Reactions
Abstract
Glossary
2.12.1 Introduction
2.12.2 Reformatsky Reagent
2.12.3 Reaction with Aldehyde and Ketone Substrates
2.12.4 Reaction with Other Substrates
2.12.5 Blaise Reaction
References
2.13 The Henry (Nitroaldol) Reaction
Abstract
Glossary
2.13.1 Introduction
2.13.2 Synthetic Application of Henry Reaction
2.13.3 Stereoselective Henry Reaction
2.13.4 Synthetic Application in Domino Reactions
2.13.5 Outlook
References
2.14 Other Condensation Reactions (Knoevenagel, Perkin, Darzens)
Abstract
2.14.1 Introduction
2.14.2 Knoevenagel Condensation
2.14.3 Perkin Condensation
2.14.4 Darzens Condensation
References
2.15 Metal Homoenolates
Abstract
Glossary
2.15.1 Introduction
2.15.2 Preparation and Reactivity of Metal Homoenolates
2.15.3 Homoenolates Generated by N-Heterocyclic Carbene (NHC)
2.15.4 Transition Metal-Catalyzed Nucleophilic Allylation of Carbonyls
2.15.5 Homoallylation of Carbonyls with Butenyl Carbanion Equivalent
2.15.6 Conclusion
References
2.16 The Bimolecular and Intramolecular Mannich and Related Reactions
Abstract
Glossary
2.16.1 Introduction
2.16.2 Metal-Catalyzed Mannich-Type Reactions
2.16.3 Organocatalyzed Mannich-Type Relations
References
2.17 Addition to N-Acyliminium Ions of Heteroatoms such as Oxygen, Nitrogen, Sulfur, and Selenium as Internal Nucleophiles
Abstract
Glossary
2.17.1 Introduction
2.17.2 Formation of the CC Bond: General Aspects
2.17.3 Formation of the CX Bond (X=O, N, S, and Se)
2.17.4 N-Acyliminium Cation Oxacyclization
2.17.5 Azacyclization of N-Acyliminium Cations
2.17.6 Thia- and Selenacyclization of N-Acyliminium Ions
2.17.7 Common Approaches Using Oxa-, Aza-, and Thiacyclizations
2.17.8 Common Reactions to Oxa- and Azacyclizations
2.17.9 Concluding Remarks
Acknowledgments
References
Volume 3: Carbon–Carbon Bond Formation
Introduction to Volume 3: CarbonCarbon Bond Formation
3.01 Alkylations of Enols and Enolates
Abstract
Glossary
3.01.1 Introduction
3.01.2 Formation and Reactivity of Enolates
3.01.3 Diastereoselective Enolate Alkylations
3.01.4 Enantioselective Enolate Alkylation
3.01.5 Miscellaneous
3.01.6 Conclusion
References
3.02 Organolithium Compounds Bearing a Phenyl-, a Vinyl-, and/or a Seleno Group on their Carbanionic Centers: Synthesis by Se/Li Exchange and Unusual Synthetic Applications
Abstract
3.02.1 Generalities
3.02.2 Reactivity of Selenides and Functionalized Selenides toward Organolithiums
3.02.3 Reactivity of Selenides and Functionalized Selenides toward Elemental Lithium and Metal Arenides
3.02.4 Reactivity of Benzyllithiums: Exceptional Family of Organometallics
3.02.5 Conclusion
References
3.03 Alkylation of α-Sulfur-Containing Carbanions
Abstract
3.03.1 Introduction
3.03.2 Alkylation of α-Thiocarbanions
3.03.3 Alkylation of α-Sulfinyl Carbanions
3.03.4 Alkylation of α-Sulfonyl Carbanions
3.03.5 Alkylations of Sulfoximinoyl Carbanions
3.03.6 Alkylation of Sulfonates, Sulfonamides, and Sulfur Ylides
3.03.7 Alkylation of Carbanions Bearing Two Geminal Sulfur Atoms
References
3.04 Alkylations of Nonstabilized Carbanions
Abstract
Glossary
3.04.1 Introduction
3.04.2 Generation and Nucleophilic Displacement of Alkyl and Alkenyl Polar Organometallics
3.04.3 Allylation of Nonstabilized (Hard) Nucleophiles
3.04.4 Carbometalations and Related Reactions
3.04.5 Transition Metal-Catalyzed Cross-Coupling Alkylations with Zn- and Mg–Alkyl Carbanions
References
3.05 Polyene Cyclizations
Abstract
3.05.1 Introduction
3.05.2 Brønsted Acid-Catalyzed Cyclizations
3.05.3 Epoxide-Based Openings
3.05.4 Other Functional Groups for Initiation
3.05.5 Metal-Mediated Polyene Cyclizations
3.05.6 Halonium-Initiated Cyclizations
3.05.7 Radical-Initiated Cyclizations
References
3.06 Transannular Electrophilic Cyclizations
Abstract
Glossary
3.06.1 Introduction
3.06.2 Eight-Membered Rings
3.06.3 Nine-Membered Rings
3.06.4 Ten-Membered Rings
3.06.5 Eleven-Membered Rings
3.06.6 Other Rings
3.06.7 Formation of Carbon–Heteroatom Bonds
References
3.07 Coupling Reactions Between sp3-Carbon Centers
Abstract
3.07.1 Introduction
3.07.2 Homocoupling Reactions
3.07.3 Direct Cross-Coupling
3.07.4 Transition Metal-Catalyzed Cross-Coupling
References
3.08 Coupling Reactions Between sp3 and sp2 Carbon Centers
Abstract
Glossary
3.08.1 Introduction
3.08.2 Copper-Catalyzed or -Mediated Coupling Reactions
3.08.3 Palladium-Catalyzed Coupling Reactions
3.08.4 Nickel-Catalyzed Coupling Reactions
3.08.5 Cobalt-Catalyzed Coupling Reactions
3.08.6 Iron-Catalyzed Coupling Reactions
References
3.09 Coupling Reactions Between C(sp2) and C(sp) Carbon Centers
Abstract
Glossary
3.09.1 General Introduction
3.09.2 Transition Metal-Catalyzed Coupling of Terminal and Masked Alkynes with C(sp2)-Halides
3.09.3 Transition Metal-Catalyzed Coupling of C(sp)-Metal Reagents with C(sp2)-Halides and Pseudohalides
3.09.4 Transition Metal-Catalyzed Coupling of C(sp2)-Metal Reagents with C(sp)-Halides and Pseudohalides
3.09.5 Domino Reactions Involving C(sp2)–C(sp) Coupling as the Key Step
References
3.10 Coupling Reactions Between sp Carbon Centers
Abstract
Glossary
3.10.1 Introduction
3.10.2 Oxidative Coupling Reactions of Terminal Alkynes
3.10.3 Coupling Reactions of Terminal Alkynes and 1-Haloalkynes
3.10.4 Oxidative Homocoupling of Organometallic Alkynides
3.10.5 Coupling of Organometallic Alkynides and 1-Haloalkynes
3.10.6 Decarboxylative Coupling of Propiolic Acids
3.10.7 Elimination Reactions of Haloolefins
3.10.8 Applications
References
3.11 Pinacol Coupling Reactions
Abstract
Glossary
3.11.1 Introduction
3.11.2 Reagents for the Pinacol Coupling Reaction
3.11.3 Pinacol Coupling Reactions in Natural Product Synthesis