Stereoselective organocatalysis : bond formation methodologies and activation modes / / edited by Ramón Ríos Torres

• Record Nr.: UNINA9910826359203321
• Pubbl/distr/stampa: Hoboken, N.J., : Wiley, c2013
• ISBN: 1-118-60475-X; 1-118-60474-1
• Edizione: [1st ed.]
• Descrizione fisica: 1 online resource (676 p.)
• Classificazione: SCI013040
• Altri autori (Persone): Ríos TorresRamón
• Disciplina: 547/.215
• Soggetti: Catalysis; Chemistry, Organic; Stereochemistry
• Lingua di pubblicazione: Inglese
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Note generali: Description based upon print version of record.
• Nota di bibliografia: Includes bibliographical references and index.
• Nota di contenuto: STEREOSELECTIVE ORGANOCATALYSIS: Bond Formation Methodologies and Activation Modes; CONTENTS; PREFACE; CONTRIBUTORS; 1. INTRODUCTION: A HISTORICAL POINT OF VIEW; REFERENCES; 2. ACTIVATION MODES IN ASYMMETRIC ORGANOCATALYSIS; 2.1. INTRODUCTION; 2.2. COVALENT ORGANOCATALYSIS; 2.2.1. Aminocatalysis; 2.2.2. Carbene Catalysis; 2.2.3. Lewis Base Organocatalysis; 2.3. NONCOVALENT ORGANOCATALYSIS; 2.3.1. Hydrogen-Bonding Activation; 2.3.2. Brønsted Base and Bifunctional Catalysis; 2.3.3. Phase-Transfer and Asymmetric Countercation-Directed Catalysis; NOTE ADDED IN PROOF; ACKNOWLEDGMENTS; REFERENCES; 3. C-C BOND FORMATION BY ALDOL REACTION3.1. INTRODUCTION; 3.2. INTRAMOLECULAR ALDOL REACTIONS; 3.3. KETONES AS DONORS; 3.3.1. β-Hydroxy Ketones; 3.3.2. Aldols with Two Stereogenic Centers Formed in the Aldol Reaction; 3.4. ALDEHYDES AS DONORS: CROSS-ALDOL REACTION; 3.4.1. Aldols with Two Stereogenic Centers Formed in the Cross-Aldol Reaction; 3.5. KETONE-KETONE; 3.5.1. Tertiary b-Hydroxy Ketones; 3.5.2. Anti-Aldols with a Quaternary Stereocenter; 3.5.3. syn-Aldols with a Quaternary Stereocenter; 3.6. OTHER CATALYSTS; 3.7. BRØNSTED ACID-CATALYZED ASYMMETRIC ALDOL REACTION; 3.8. CONCLUSIONS; REFERENCES4. EXAMPLES OF METAL-FREE DIRECT CATALYTIC ASYMMETRIC MANNICH-TYPE REACTIONS USING AMINOCATALYSIS; 4.1. INTRODUCTION; 4.2. METAL-FREE CATALYSIS; 4.3. CONCLUSION; REFERENCES AND NOTES; 5. C-C BOND FORMATION BY MICHAEL REACTION; 5.1. INTRODUCTION; 5.2. SIMPLE SUBSTRATES; 5.2.1. Michael Addition of Aldehydes; 5.2.2. Michael Addition of Ketones; 5.2.3. Michael Addition of Nitroalkanes; 5.2.4. Michael Addition of Activated Methylenes; 5.3. SPECIAL SCAFFOLD; 5.3.1. Oxindoles; 5.3.2. Benzofuran-2(3H)-ones; 5.3.3. Oxazolones; 5.3.4. Nitro-ethenamine; 5.3.5. β-Carbonyl Heteroaryl Sulfones; 5.4. NEW APPROACH5.4.1. Intramolecular Michael Reaction; 5.4.2. Mukaiyama-Michael Reactions; 5.4.3. Desymmetric Michael Reactions; 5.4.4. Direct Vinylogous Michael Reactions; 5.5. MISCELLANEOUS; 5.6. CONCLUSION; REFERENCES; 6. C-C BOND FORMATION BY DIELS-ALDER AND OTHER PERICYCLIC REACTIONS; 6.1. INTRODUCTION; 6.2. DIELS-ALDER REACTIONS; 6.3. HETERO-DIELS-ALDER REACTIONS; 6.4. [3+2] CYCLOADDITION REACTIONS; 6.5. [2+2] CYCLOADDITION REACTIONS; 6.6. ELECTROCYCLIZATIONS; 6.7. SIGMATROPIC REACTIONS; 6.8. ENE REACTIONS; 6.9. OUTLOOK; REFERENCES; 7. N-HETEROCYCLIC CARBENE-CATALYZED C-C BOND FORMATION7.1. INTRODUCTION; 7.2. BENZOIN CONDENSATION OF ALDEHYDES; 7.2.1. Self-Benzoin Condensation; 7.2.2. Cross-Benzoin Reaction; 7.2.3. Aza-Cross-Benzoin Reaction; 7.3. STETTER REACTION OF ALDEHYDES; 7.3.1. Intramolecular Stetter Reaction; 7.3.2. Intermolecular Stetter Reaction; 7.4. CROSS-COUPLING REACTIONS OF ALDEHYDES WITH ACTIVATED HALIDES; 7.5. REACTION OF SILYLATED REAGENTS; 7.6. REARRANGEMENT OF ENOL ESTERS; 7.7. REACTIONS OF MICHAEL ACCEPTORS; 7.8. MICHAEL ADDITIONS; 7.9. EXTENDED UMPOLUNG OF FUNCTIONALIZED ALDEHYDES; 7.10. FORMAL CYCLOADDITIONS OF KETENES
• Sommario/riassunto: Sets forth an important group of environmentally friendly organic reactions With contributions from leading international experts in organic synthesis, this book presents all the most important methodologies for stereoselective organocatalysis, fully examining both the activation mode as well as the type of bond formed. Clear explanations guide researchers through all the most important methods used to form key chemical bonds, including carbon-carbon (C-C), carbon-nitrogen (C-N), and carbon-halogen (C-X) bonds. Moreover, readers will discover how the use of non-metallic catalys