| Description |
1 online resource |
| Contents |
Machine generated contents note: 1.1. Introduction / Hélène Pellissier -- 1.2. Asymmetric Domino Reactions using Chiral Carbohydrate Derivatives / Hélène Pellissier -- 1.2.1. Stereocontrolled Domino Reactions of Chiral Carbohydrate Derivatives / Hélène Pellissier -- 1.2.2. Enantioselective Domino Reactions Catalyzed by Chiral Carbohydrate Derivatives / Hélène Pellissier -- 1.3. Conclusions / Hélène Pellissier -- References / Hélène Pellissier -- 2.1. Introduction / Benjamin Voigt / Rainer Mahrwald -- 2.2.C-Glycosides / Benjamin Voigt / Rainer Mahrwald -- 2.3. Amine-Catalyzed Knoevenagel-Additions / Benjamin Voigt / Rainer Mahrwald -- 2.4. Multicomponent Reactions / Benjamin Voigt / Rainer Mahrwald -- 2.5. Amine-Catalyzed Cascade Reactions of Ketoses with 1,3-Dicarbonyl Compounds / Benjamin Voigt / Rainer Mahrwald -- 2.6. Conclusions / Benjamin Voigt / Rainer Mahrwald -- References / Benjamin Voigt / Rainer Mahrwald -- 3.1. Introduction / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2. Bernet-Vasella Reaction / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2.1. Domino Reductive Fragmentation/Reductive Amination / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2.2. Domino Reductive Fragmentation/Barbier-Type Allylation / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2.3. Domino Reductive Fragmentation/Barbier-Type Propargylation / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2.4. Domino Reductive Fragmentation/Vinylation / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2.5. Domino Reductive Fragmentation/Alkylation / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2.6. Domino Reductive Fragmentation/Olefination / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.2.7. Domino Reductive Fragmentation/Nitromethylation / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.3. Reductive Ring Contraction / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.3.1. Ring Opening/Ketyl-Olefin Annulation / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.3.2. Ring Opening/Intramolecular Carbonyl Alkylation / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 3.4. Conclusions / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- References / Raquel G. Soengas / Sara M. Tomé / Artur M.S. Silva -- 4.1. Introduction / Vasco Cachatra / Amélia P. Rauter -- 4.2. Domino Reactions Toward Butenolides Fused to Six-Membered Ring Sugars and Thio Sugars / Vasco Cachatra / Amélia P. Rauter -- 4.3. Exploratory Chemistry for Amino Sugars' Domino Reactions / Vasco Cachatra / Amélia P. Rauter -- 4.4. Domino Reactions Toward Sugar Ring Contraction / Vasco Cachatra / Amélia P. Rauter -- 4.4.1. Pyrano-Furano Ring Contraction / Vasco Cachatra / Amélia P. Rauter -- 4.4.2. Ring Contraction of Furans to Oxetanes / Vasco Cachatra / Amélia P. Rauter -- 4.5. Macrocyclic Bislactone Synthesis via Domino Reaction / Vasco Cachatra / Amélia P. Rauter -- 4.6. Sugar Deoxygenation by Domino Reaction / Vasco Cachatra / Amélia P. Rauter -- 4.7. Conclusions / Vasco Cachatra / Amélia P. Rauter -- References / Vasco Cachatra / Amélia P. Rauter -- 5.1. Introduction / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.2.(5,6-Dihydro-1,4-dithiin-2-y1)Methanol: Not Simply a Homologating Agent / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.3. Sulfur-Assisted Multistep Processes and Their Use in the De Novo Synthesis of Glycostructures / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.3.1. Three Steps in One Process: Double Approach to 4-Deoxy L-(and D- )-Hexoses / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.3.2. Five Steps in One Process: The Domino Way to L-Hexoses (and Their Derivatives) / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.3.3. Up to Six Steps in One Process: 4'-Substituted Nucleoside Synthesis / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.3.4. Eight Steps in One Process: Beyond Achmatowicz Rearrangement / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.4. Concluding Remarks / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 5.5. Acknowledgments / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- References / Daniele D'Alonzo / Giovanni Palumbo / Annalisa Guaragna -- 6.1. Introduction / Zbigniew J. Witczak / Roman Bielski -- 6.2. Classification and Reaction Mechanism / Zbigniew J. Witczak / Roman Bielski -- 6.3. Conclusions / Zbigniew J. Witczak / Roman Bielski -- References / Zbigniew J. Witczak / Roman Bielski -- 7.1. Introduction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2. Convertible Isocyanides / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.1. CIC Employed in the Ugi Reaction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.2. Resin-Bound CICs / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.3. CIC Employed in the Ugi-Smile Reaction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.4. CIC Employed in the Joullié-Ugi Reaction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.5. CIC Employed in the Passerini Reaction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.6. CIC Employed in the Groebke-Blackburn-Bienaymé Reaction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.7. CIC Employed in the Diels-Alder Reaction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.8. Monosaccharide Isocyanides Employed in the Ugi and Passerini Reaction / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.2.9. Methyl isocyanide in the Preparation of the Hydroxy DKP Thaxtomin A / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 7.3. Conclusions / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- References / Soumava Santra / Tonja Andreana / Jean-Paul Bourgault / Peter R. Andreana -- 8.1. Introduction / Daniel B. Werz -- 8.2. Spiroketals via a Domino Oxidation/Rearrangement Sequence / Daniel B. Werz -- 8.3. Chromans and Isochromans via Domino Carbopalladation/Carbopalladation/Cyclization Sequence / Daniel B. Werz -- References / Daniel B. Werz -- 9.1. Introduction / Roman Bielski / Zbigniew J. Witczak -- 9.2. Classification / Roman Bielski / Zbigniew J. Witczak -- 9.3. Chapman Rearrangement / Zbigniew J. Witczak / Roman Bielski -- 9.4. Hofmann Rearrangement / Zbigniew J. Witczak / Roman Bielski -- 9.5. Cope Rearrangement / Zbigniew J. Witczak / Roman Bielski -- 9.6. Ferrier Rearrangement / Roman Bielski / Zbigniew J. Witczak -- 9.7. Claisen Rearrangement / Zbigniew J. Witczak / Roman Bielski -- 9.8. Overman Rearrangement / Roman Bielski / Zbigniew J. Witczak -- 9.9. Baeyer-Villiger Rearrangement / Zbigniew J. Witczak / Roman Bielski -- 9.10. Ring Contraction / Roman Bielski / Zbigniew J. Witczak -- 9.11. Conclusions / Zbigniew J. Witczak / Roman Bielski -- References / Zbigniew J |
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Witczak / Roman Bielski -- 10.1. Introduction / Agnieszka Gajewska / Anna Osuch-Kwiatkowska / Stawomir Jarosz / Maciej Cieplak -- 10.2. Rearrangements Without Changing the Sugar Skeleton / Agnieszka Gajewska / Anna Osuch-Kwiatkowska / Stawomir Jarosz / Maciej Cieplak -- 10.3. Rearrangements Connected with the Change of Sugar Unit(s) / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.4. Rearrangements Changing the Structure of a Sugar Skeleton / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.5. Rearrangement of the Sugar Skeleton Discovered En Route to Higher-Carbon Sugars / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.5.1. Synthesis of Higher-Carbon Sugars by the Wittig-Type Methodology / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.5.2. The AcetyleneNinyltin Methodology in the Synthesis of HCS / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.5.3. The Allyltin Methodology in the Synthesis of HCS / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.5.4. Rearrangement of the Structure of HCS / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.5.5. Synthesis of Polyhydroxylated Carbocyclic Derivatives with Large Rings / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 10.6. Conclusions / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- Acknowledgments / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- References / Stawomir Jarosz / Anna Osuch-Kwiatkowska / Agnieszka Gajewska / Maciej Cieplak -- 11.1. Introduction / Roman Bielski / Zbigniew J. Witczak -- 11.2. Additions to the Double Bond of the Enone System Leading to the Formation of New Rings / Roman Bielski / Zbigniew J. Witczak -- 11.3. Reductions of the Carbonyl Group Followed by Various Reactions of the Formed Alcohol / Roman Bielski / Zbigniew J. Witczak -- 11.4. Functionalization of the Carbonyl Group by Forming Carbon-Nitrogen Double Bonds (Oximes, Enamines, Hydrazines) / Roman Bielski / Zbigniew J. Witczak -- 11.5. Additions (But Not Cycloadditions) (Particularly Michael Additions) to the Double Bond of the Enone / Zbigniew J. Witczak / Roman Bielski -- 11.6. Enzymatic Reactions of Levoglucosenone / Roman Bielski / Zbigniew J. Witczak -- 11.7. High-Tonnage Products from Levoglucosenone / Roman Bielski / Zbigniew J. Witczak -- 11.7.1. Overman and Allylic Xanthate Rearrangement / Roman Bielski / Zbigniew J. Witczak -- 11.8. Conclusions / Roman Bielski / Zbigniew J. Witczak -- References / Roman Bielski / Zbigniew J. Witczak -- 12.1. Introduction / Vikram Basava / Emi Hanawa / Cecilia H. Ma |
| Summary |
The book consists of a brief introduction, a foreward provided by professor Danishefsky of Columbia University, and about 14 - 16 chapters, each written by one or two eminent scholars/authors describing their recent research in the area of either domino reactions or intramolecular rearrangements in carbohydrate chemistry. Three or four chapters will be reviews. The domino (cascade, tandem) reactions are always intramolecular. They are usually very fast, clean and offer highly complex structures in a one pot process. Intramolecular rearrangements offer very similar advantages and often lead to highly complex products as well. Although many recently isolated carbohydrates fulfill various sophisticated functions, their structures are often very complex. The editors cover the broadest scope of novel methodologies possible. All the synthetic and application aspects of domino/cascade reactions are explored in this book. A second theme that will be covered is intramolecular rearrangement, which is also fast, stereoselective, and often constitutes one or more steps of domino /cascade process. Selected examples of intramolecular rearrangements are presented. Together, both processes offer an elegant and convenient approach to the synthesis of many complex molecules, which are normally difficult to synthesize via alternative routes. It appears that domino and intramolecular rearrangements are ideally suited to synthesize certain specific modified monosaccharides. What is particularly important is that both processes are intermolecular and almost always yield products with very well-defined stereochemistry. This high definition is absolutely crucial when synthesizing advanced, modified mono and oligosaccharides. The choice of contributors reflects an emphasis on both therapeutic and pharmacological aspects of carbohydrate chemistry |
| Bibliography |
Includes bibliographical references |
| Notes |
Print version record and CIP data provided by publisher |
| Subject |
Glycosides -- Chemical warfare -- Laboratory manuals
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Glycosides -- chemistry
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Chemistry Techniques, Synthetic -- methods
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SCIENCE -- Life Sciences -- Biochemistry.
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| Genre/Form |
Laboratory manuals
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Laboratory manuals.
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Manuels de laboratoire.
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| Form |
Electronic book
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| Author |
Witczak, Zbigniew J., 1947- editor.
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Bielski, Roman, 1946- editor.
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| LC no. |
2015040811 |
| ISBN |
9781119044390 |
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1119044391 |
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9781119044239 |
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1119044235 |
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9781119044222 |
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1119044227 |
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1119044200 |
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9781119044208 |
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