Details

Asymmetric Synthesis II


Asymmetric Synthesis II

More Methods and Applications
1. Aufl.

von: Mathias Christmann, Stefan Bräse

111,99 €

Verlag: Wiley-VCH
Format: EPUB
Veröffentl.: 17.04.2013
ISBN/EAN: 9783527672592
Sprache: englisch
Anzahl Seiten: 430

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Beschreibungen

<p>After the overwhelming success of <i>Asymmetric Synthesis - The Essentials</i>, displaying a broad range of organic asymmetric syntheses, this is the <i>second edition</i> with latest subjects and authors. While the aim of the <i>first edition</i> was mainly to honor the achievements of the pioneers in asymmetric syntheses, the aim of this new edition was bringing the current developments, especially from younger colleagues, to the attention of students. The format of the book remained unchanged, i.e. short conceptual overviews by young leaders in their field including a short biography of the authors. The growing multidisciplinary research within chemistry is reflected in the selection of topics including metal catalysis, organocatalysis, physical organic chemistry, analytical chemistry, and its applications in total synthesis, materials research and industry.</p> <p>The prospective reader of this book is a graduate or undergraduate student of advanced organic chemistry as well as the industrial chemist who wants to get a brief update on the current developments in the field.</p>
CATALYTIC ENANTIOSELECTIVE ALKYLATION OF PROCHIRAL KETONE ENOLATES <br> Background <br> Strategy and Results <br> Asymmetric Allylic Alkylation in Total Synthesis <br> Conclusions <br> <br> POINT-TO-PLANAR CHIRALITY TRANSFER IN TOTAL SYNTHESIS: SCALABLE AND PROGRAMMABLE SYNTHESIS OF HAOUAMINE A AND ITS ATROPISOMER <br> Introduction <br> Synthetic Strategy Featuring Point-to-Planar Chirality Transfer <br> Programmable Synthesis of Haouamine A and Its Atropisomer <br> <br> TETHERED AMINOHYDROXYLATION <br> Introduction and Background <br> Tethered Aminohydroxylation <br> Amide-Based Reoxidants<br> Evidence for the Mechanism of the TA Reaction<br> Applications in Organic Synthesis <br> Conclusion and Future Work <br> <br> ORGANOCATALYZED TRANSFORMATIONS OF A, B-UNSATURATED CARBONYL COMPOUNDS THROUGH IMINIUM ION INTERMEDIATES <br> <br> THE RENAISSANCE OF SILICON-STEREOGENIC SILANES: A PERSONAL ACCOUNT <br> Background <br> Results <br> Conclusion <br> <br> ASYMMETRIC DIENAMINE ACTIVATION <br> Introduction<br> Historic Background <br> Results <br> Conclusion <br> <br> ASYMMETRIC BR?NSTED ACID CATALYSIS <br> Introduction and Background <br> Strategy <br> Results <br> Summary <br> <br> QUATERNARY STEREOGENIC CENTERS BY ENANTIOSELECTIVE B-CARBON ELIMINATIONS FROM TERT-CYCLOBUTANOLS <br> Background <br> Objective: Enantioselective Formation of Quaternary Stereogenic Centers in Combination with Reactive Alkyl-Rhodium<br> Intermediates <br> Selective Generation of the Alkyl-Rhodium Species and Its Downstream Reactivities <br> <br> TOTAL SYNTHESIS OF OSELTAMIVIR AND ABT-341 USING ONE-POT TECHNOLOGY <br> Introduction <br> Results <br> Conclusions <br> <br> ENANTIOSELECTIVE ANNULATIONS WITH CHIRAL N-MESITYL N-HETEROCYCLIC CARBENES <br> Introduction <br> Catalytic Generation of Chiral Enolate Equivalents <br> Catalytic Generation of Homoenolate Equivalents <br> Enantioselective Cascade Reactions Catalyzed by Chiral N-Heterocyclic Carbenes <br> Catalytic Annulations via a, ?-Unsaturated Acyl Azoliums <br> Conclusions <br> <br> ASYMMETRIC COUNTERANION-DIRECTED CATALYSIS (ACDC) <br> Concept <br> Application of ACDC to Organocatalysis <br> Application of ACDC to Transition Metal Catalysis <br> Application of ACDC to Lewis Acid Catalysis <br> <br> ENANTIOSELECTIVE ORGANO-SOMO CATALYSIS: A NOVEL ACTIVATION MODE FOR ASYMMETRIC SYNTHESIS <br> Background <br> Objective <br> Results <br> <br> ENANTIOSELECTIVE PASSERINI REACTION <br> Introduction <br> Background <br> Results <br> Conclusion and Perspective <br> <br> RAPID ENANTIOMERIC EXCESS DETERMINATION <br> <br> ASYMMETRIC CATALYSIS OF REVERSIBLE REACTIONS <br> Thermochemistry of Asymmetric Catalyses Close to the Equilibrium <br> Kinetic Modeling of a Reversible Asymmetric Catalytic Reaction <br> Case Study: a Reversible Asymmetric Organocatalytic Reaction <br> Conclusions <br> <br> EXPLOITING FLUORINE CONFORMATIONAL EFFECTS IN ORGANOCATALYST DESIGN: THE FLUORINE?IMINIUM ION GAUCHE EFFECT <br> <br> DUTCH RESOLUTION <br> <br> CONSTRUCTION OF ANTI-ME-OH VICINAL RELATIONSHIPS IN POLYKETIDES <br> Introduction <br> Marshall -<br> Tamaru Reaction <br> Conclusions <br> <br> PHOTOSWITCHABLE GENERAL BASE CATALYSTS <br> Introduction and Background <br> Strategy and Results <br> Outlook <br> <br> ASYMMETRIC HALONIUM ADDITION TO OLEFINS <br> Introduction <br> Intramolecular Lactonizations, Etherifications, and Aminations <br> Polyene Cyclizations <br> Intermolecular Additions to Alkenes <br> Conclusion <br> <br> CATALYTIC ASYMMETRIC GOSTELI -<br> CLAISEN REARRANGEMENT (CAGC) <br> <br> BIOMIMETIC TOTAL SYNTHESIS OF THE PENIFULVIN FAMILY <br> Introduction <br> The Penifulvin Family: Isolation and Biogenetic Origin <br> Total Syntheses of Penifulvins A, B, and C <br> Summary <br> <br> CATALYST-CONTROLLED 1,3-POLYOL SYNTHESES <br> <br> ENANTIOSELECTIVE CARBONYL ALLYLATION AND CROTYLATION FROM THE ALCOHOL OXIDATION LEVEL VIA C?C BOND FORMING TRANSFER HYDROGENATION <br> Introduction and Background <br> Strategy<br> Results <br> <br> STEREOSELECTIVE SYNTHESIS WITH HYPERVALENT IODINE REAGENTS <br> <br> ASYMMETRIC GOLD-CATALYZED REACTIONS <br> Introduction <br> Diphosphine-Gold Complexes in Enantioselective Catalysis <br> Monophosphine-Gold Complexes in Enantioselective Catalysis <br> <br> ASYMMETRIC CATALYSIS IN THE TOTAL SYNTHESIS OF LIPIDS AND POLYKETIDES <br> Background<br> Tuberculostearic Acid: One Isolated Methyl Group <br> Ant Pheromones: Vicinal Methyl Branches <br> Deoxypropionates: 1,3-Methyl Arrays<br> Membrane-Spanning Lipids: 1,4-Dimethyl Units <br> Saturated Isoprenoids: 1,5-Methyl Arrays <br> <br> THE EVOLVING ROLE OF BIOCATALYSIS IN ASYMMETRIC SYNTHESIS <br> Background - First- and Second-Generation Biotransformations <br> Results -<br> Third-Generation Biotransformations<br> Conclusions and Future Perspectives <br> <br> BIFUNCTIONAL THIOUREA CATALYSTS <br> Background <br> Results <br> <br> <br> CATALYTIC ASYMMETRIC (4 + 3) CYCLOADDITIONS USING ALLENAMIDES <br> Introduction and Background <br> Strategy <br> Results <br> Conclusion <br> <br> APPLICATION OF THE ACHMATOWICZ REARRANGEMENT FOR THE SYNTHESIS OF OLIGOSACCHARIDES <br> Introduction <br> De novo Approach to Carbohydrates <br> An Iterative Pd-Catalyzed Glycosylation and Bidirectional Postglycosylation <br> Application to the Synthesis of the Anthrax Tetrasaccharide <br> <br> ASYMMETRIC C -<br> C BOND FORMATION USING CHIRAL PHOSPHORIC ACID <br> Background <br> Results <br> Conclusions and Future Perspectives <br> <br> ASYMMETRIC C -<br> H BOND FUNCTIONALIZATION <br> Background <br> Results <br> Conclusions and Future Perspectives <br> <br> ASYMMETRIC C -<br> C BOND FORMATION USING CHIRAL GUANIDINE CATALYSTS <br> Background <br> Catalyst Design and Results <br> <br> ENANTIOSELECTIVE SYNTHESIS OF LACTONES VIA RH-CATALYZED KETONE HYDROACYLATION <br> Background and Introduction <br> Strategy and Results <br> Conclusions and Future Directions <br> <br> RADICAL HALOALKYLATION <br> <br> ASYMMETRIC HYDROVINYLATION OF ALKENES <br> Introduction <br> New Protocols for the Heterodimerization of Ethylene/Propylene and Vinylarenes, 1,3-Dienes, and Norbornene <br> Catalytic Asymmetric Hydrovinylation Reactions: Effects of Hemilabile Ligands <br> All-Carbon Quaternary Centers via Catalytic Asymmetric HV <br> Hydrovinylation (HV) of 1,3-Dienes and Asymmetric Variations <br> Asymmetric Hydrovinylation of Unactivated Linear 1,3-Dienes Using Co(II) Catalysis <br> Scope and Applications of Hydrovinylation Reactions: Exocyclic Stereocontrol <br> A Stereoselective Route to either Steroid-C20(S) or -C20(R) Derivatives <br> Asymmetric Hydrovinylation of Strained Alkenes <br> Conclusions and Future Perspectives <br> <br> HETEROCYCLE CONSTRUCTION VIA ASYMMETRIC RHODIUM-CATALYZED CYCLOADDITIONS <br> Background <br> Strategy <br> Results <br> Application to Other Reactions <br> Conclusion and Future Perspectives <br> <br> N-HETEROCYCLIC CARBENE-CATALYZED ALDOL DESYMMETRIZATIONS <br> Introduction <br> Strategy and Results <br> Application to the Syntheses of Bakkenolides I, J, and S <br> Conclusion <br> <br> STRATEGIES FOR THE ASYMMETRIC TOTAL SYNTHESIS OF NATURAL PRODUCTS: `'CHIRAL POOL' VERSUS CHIRAL CATALYSTS <br> Introduction <br> Catalytic Stereoselective Total Synthesis <br> Natural Product Synthesis Starting from Chiral, Nonracemic Starting Materials <br> Conclusion <br> <br> DYNAMIC KINETIC ASYMMETRIC TRANSFORMATIONS INVOLVING CARBON -<br> CARBON BOND CLEAVAGE <br> Background <br> Donor -<br> Acceptor Cyclopropanes as DYKAT Substrates <br> Lewis Acid Catalysis <br> Palladium Catalysis <br> Deracemization of Tertiary Propargyl-Allyl Alcohols via Rhodium-Catalyzed Sequential Rearrangement/Enantioselective Conjugate Addition <br> Conclusion <br> <br> IRON-CATALYZED ALLYLIC SUBSTITUTIONS <br> Allylic Substitutions Catalyzed by the Hieber-Anion [Fe(CO)3(NO)]- <br> Allylic Substitutions Catalyzed by Fe2(CO)9 <br> <br> ASYMMETRIC CONIA-ENE CARBOCYCLIZATIONS <br> Introduction and Background: the Conia-ene Reaction <br> Strategy: Organo/Metal Cooperative Catalysis <br> Results <br> <br> TACTICS AND STRATEGIES IN THE TOTAL SYNTHESIS OF CHLOROSULFOLIPIDS <br> Background <br> Stereoselective Synthesis of vic-Dichloride Fragments <br> Total Synthesis of Hexachlorosulfolipid <br> Conclusions <br> <br> LINEAR FREE ENERGY RELATIONSHIPS (LFERS) IN ASYMMETRIC CATALYSIS <br> Introduction and Background <br> Hammett Electronic Parameters and Their Application to (salen)Mn(III)-Catalyzed Asymmetric Epoxidation Reactions <br> Relating Br?nsted Acidity to Enantiomeric Ratio in an Asymmetric Hydrogen-Bond-Catalyzed Diels-Alder Reaction <br> An LFER Describing the Influence of Steric Bulk in a Nozaki?Hiyama -<br> Kishi Asymmetric Allylation of Acetophenone <br> Correlating Quadrupole Moment to Enantioselectivity in Cation-p-Mediated Asymmetric Polycyclization <br> Simultaneously Correlating Hammett and Charton Parameters to Enantioselectivity in Two-Dimensional Free Energy Relationships <br> Conclusions <br> <br> ASYMMETRIC DIAMINATION OF ALKENES <br> Introduction and Background <br> Strategy <br> Results <br> <br> ENZYMATIC ASYMMETRIC SYNTHESIS OF TERTIARY ALCOHOLS <br> Introduction <br> YerE - a Unique ThDP-Dependent Enzyme <br> Hydroxynitrile Lyases <br> Conclusion <br> <br> OXIDATIVE DEAROMATIZATION AND ORGANOCATALYTIC DESYMMETRIZATION <br> Introduction <br> Desymmetrization of Cyclohexadienones <br> A One-Pot Oxidative Dearomatization and Catalytic Desymmetrization <br> Oxo- and Aza-Michael Additions <br> Further One-Pot Methods for Oxidative Dearomatization and Catalytic Desymmetrization <br> Alkylative Dearomatization <br> Summary <br> <br> TOTAL SYNTHESIS OF ALL (-)-AGELASTATIN ALKALOIDS <br> Introduction <br> Biosynthetically Inspired Plan for Total Synthesis <br> Total Synthesis of the Agelastatin Alkaloids <br> <br>
<p><b>Stefan Brase</b> studied chemistry in Bangor, UK, Marseille, France, and Gottingen, Germany, where he gained his doctorate under Armin de Meijere in 1995. After post-doctoral appointments at Uppsala University, Sweden under J.-E. Backvall and The Scripps Research Institute, La Jolla, USA with K. C. Nicolaou, he began his research career at the RWTH Aachen with Dieter Enders in 1997, obtaining his lecturing qualification in 2001. He became a professor at the University of Bonn that same year and since 2003 he has been Full Professor at the Karlsruhe Institute of Technology. Professor Brase has more than 250 publications to his name and is a recipient of the ORCHEM award. His research interests include methods in drug discovery, combinatorial chemistry with a focus on the synthesis of biologically active compounds, total synthesis of natural products and nanotechnology.</p> <p><b>Mathias Christmann</b> studied chemistry at the Technical University of Braunschweig and received a PhD from the Leibniz University of Hannover with Markus Kalesse. After postdoctoral research with Craig J. Forsyth at the University of Minnesota, USA, he joined the RWTH Aachen University as a Liebig Fellow of the Fonds der Chemischen Industrie, working towards his lecturing qualifi cation under Dieter Enders. In 2008, he was appointed Associate Professor at the Dortmund University of Technology, where he lectures in organic chemistry. Professor Christmann's research interests include organocatalysis, natural products synthesis and sustainable chemistry.</p>
After the overwhelming success of 'Asymmetric Synthesis - The Essentials', narrating the colorful history of asymmetric synthesis, this<br> is the second edition with latest subjects and authors. While the aim of the first edition was mainly to honor the achievements of the pioneers<br> in asymmetric syntheses, the aim of this new edition was bringing the current developments, especially from younger colleagues, to the<br> attention of students. The format of the book remained unchanged, i.e. short conceptual overviews by young leaders in their field including<br> a short biography of the authors. The growing multidisciplinary research within chemistry is reflected in the selection of topics including metal catalysis, organocatalysis, physical organic chemistry, analytical chemistry, and its applications in total synthesis. The prospective reader of this book is a graduate or undergraduate student of advanced organic chemistry as well as the industrial chemist who wants to get a brief update on the current developments in the field.

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