Asymmetric Synthesis II E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 527

Veröffentlichungsjahr: 2013

Beschreibung

After the overwhelming success of Asymmetric Synthesis - The Essentials, displaying a broad range of organic asymmetric syntheses, this 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 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.

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.

Leseprobe

Table of Contents

Related Titles

Title Page

Copyright

List of Contributors

Chapter 1: Catalytic Enantioselective Alkylation of Prochiral Ketone Enolates

Background

Strategy and Results

Asymmetric Allylic Alkylation in Total Synthesis

Conclusions

CV of Corey M. Reeves

CV of Brian M. Stoltz

References

Chapter 2: Point-to-Planar Chirality Transfer in Total Synthesis: Scalable and Programmable Synthesis of Haouamine A and Its Atropisomer

Introduction

Synthetic Strategy Featuring Point-to-Planar Chirality Transfer

Programmable Synthesis of Haouamine A and Its Atropisomer

CV of Noah Z. Burns

CV of Phil S. Baran

References

Chapter 3: Tethered Aminohydroxylation

Introduction and Background

Tethered Aminohydroxylation

Amide-Based Reoxidants

Evidence for the Mechanism of the TA Reaction

Applications in Organic Synthesis

Conclusion and Future Work

CV of Timothy J. Donohoe

CV of Stefanie Mesch

References

Chapter 4: Organocatalyzed Transformations of α, β-Unsaturated Carbonyl Compounds through Iminium Ion Intermediates

CV of Nicholas C. O. Tomkinson

CV of Julian H. Rowley

References

Chapter 5: The Renaissance of Silicon-Stereogenic Silanes: A Personal Account

Background

Results

Conclusion

CV of Martin Oestreich

CV of Andreas Weickgenannt

References

Chapter 6: Asymmetric Dienamine Activation

Introduction

Historic Background

Results

Conclusion

CV of Mathias Christmann

References

Chapter 7: Asymmetric Brønsted Acid Catalysis

Introduction and Background

Strategy

Results

Summary

CV of Iuliana Atodiresei

CV of Uxue Uria

CV of Magnus Rueping

References

Chapter 8: Quaternary Stereogenic Centers by Enantioselective β-Carbon Eliminations from tert-Cyclobutanols

Background

Objective: Enantioselective Formation of Quaternary Stereogenic Centers in Combination with Reactive Alkyl-Rhodium Intermediates

Selective Generation of the Alkyl-Rhodium Species and Its Downstream Reactivities

CV of Nicolai Cramer

CV of Tobias Seiser

Chapter 9: Total Synthesis of Oseltamivir and ABT-341 Using One-Pot Technology

Introduction

Results

Conclusions

CV of Yujiro Hayashi

CV of Hayato Ishikawa

References

Chapter 10: Enantioselective Annulations with Chiral N-Mesityl N-Heterocyclic Carbenes

Introduction

Catalytic Generation of Chiral Enolate Equivalents

Catalytic Generation of Homoenolate Equivalents

Enantioselective Cascade Reactions Catalyzed by Chiral N-Heterocyclic Carbenes

Catalytic Annulations via α, β-Unsaturated Acyl Azoliums

Conclusions

CV of Jeffrey Bode

CV of Jessada Mahatthananchai

References

Chapter 11: Asymmetric Counteranion-Directed Catalysis (ACDC)

Concept

Application of ACDC to Organocatalysis

Application of ACDC to Transition Metal Catalysis

Application of ACDC to Lewis Acid Catalysis

CV of Manuel Mahlau

CV of Prof. Dr. Benjamin List

References

Chapter 12: Enantioselective Organo-SOMO Catalysis: a Novel Activation Mode for Asymmetric Synthesis

Background

Objective

Results

CV of David W.C. MacMillan

CV of Sebastian Rendler

References

Chapter 13: Enantioselective Passerini Reaction

Introduction

Background

Results

Conclusion and Perspective

CV of Qian Wang

CV of Jieping Zhu

CV of Mei-Xiang Wang

References

Chapter 14: Rapid Enantiomeric Excess Determination

CV of Oliver Trapp

References

Chapter 15: Asymmetric Catalysis of Reversible Reactions

Thermochemistry of Asymmetric Catalyses Close to the Equilibrium

Kinetic Modeling of a Reversible Asymmetric Catalytic Reaction

Case Study: a Reversible Asymmetric Organocatalytic Reaction

Conclusions

CV of Lukas Hintermann

References

Chapter 16: Exploiting Fluorine Conformational Effects in Organocatalyst Design: The Fluorine–Iminium Ion Gauche Effect

CV of C. Sparr

CV of L. Zimmer

CV of R. Gilmour

References

Chapter 17: Dutch Resolution

CV of Richard M. Kellogg

References

Chapter 18: Construction of anti-Me-OH Vicinal Relationships in Polyketides

Introduction

Marshall–Tamaru Reaction

Conclusions

CV of Vaidotas Navickas

CV of Martin E. Maier

References

Chapter 19: Photoswitchable General Base Catalysts

Introduction and Background

Strategy and Results

Outlook

CV of Philipp Viehmann

CV of Stefan Hecht

References

Chapter 20: Asymmetric Halonium Addition to Olefins

Introduction

Intramolecular Lactonizations, Etherifications, and Aminations

Polyene Cyclizations

Intermolecular Additions to Alkenes

Conclusion

CV of Scott A. Snyder

CV of Alexandria P. Brucks

References

Chapter 21: Catalytic Asymmetric Gosteli–Claisen Rearrangement (CAGC)

CV of Julia Rehbein

CV of Martin Hiersemann

References

Chapter 22: Biomimetic Total Synthesis of the Penifulvin Family

Introduction

The Penifulvin Family: Isolation and Biogenetic Origin

Total Syntheses of Penifulvins A, B, and C

Summary

CV of Prof. Johann Mulzer

CV of Tanja Gaich

References

Chapter 23: Catalyst-Controlled 1,3-Polyol Syntheses

CV of Stefan F. Kirsch

CV of Tobias Harschneck

References

Chapter 24: Enantioselective Carbonyl Allylation and Crotylation from the Alcohol Oxidation Level via C–C Bond Forming Transfer Hydrogenation

Introduction and Background

Strategy

Results

CV of Michael Krische

CV of Joseph Moran

References

Chapter 25: Stereoselective Synthesis with Hypervalent Iodine Reagents

CV of Umar Farid

CV of Thomas Wirth

References

Chapter 26: Asymmetric Gold-Catalyzed Reactions

Introduction

Diphosphine-Gold Complexes in Enantioselective Catalysis

Monophosphine-Gold Complexes in Enantioselective Catalysis

CV of Núria Huguet

CV of Antonio M. Echavarren

References

Chapter 27: Asymmetric Catalysis in the Total Synthesis of Lipids and Polyketides

Background

Tuberculostearic Acid: One Isolated Methyl Group

Ant Pheromones: Vicinal Methyl Branches

Deoxypropionates: 1,3-Methyl Arrays

Membrane-Spanning Lipids: 1,4-Dimethyl Units

Saturated Isoprenoids: 1,5-Methyl Arrays

CV of Santiago Barroso

CV of Adriaan J. Minnaard

References

Chapter 28: The Evolving Role of Biocatalysis in Asymmetric Synthesis

Background – First- and Second-Generation Biotransformations

Results–Third-Generation Biotransformations

Conclusions and Future Perspectives

CV of Mélanie Hall

CV of Wolfgang Kroutil

CV of Kurt Faber

References

Chapter 29: Bifunctional Thiourea Catalysts

Background

Results

CV of Yoshiji Takemoto

CV of Tsubasa Inokuma

References

Chapter 30: Catalytic Asymmetric (4 + 3) Cycloadditions Using Allenamides

Introduction and Background

Strategy

Results

Conclusion

CV of Yun-Fei Du

CV of Richard P. Hsung

References

Chapter 31: Application of the Achmatowicz Rearrangement for the Synthesis of Oligosaccharides

Introduction

De novo Approach to Carbohydrates

An Iterative Pd-Catalyzed Glycosylation and Bidirectional Postglycosylation

Application to the Synthesis of the Anthrax Tetrasaccharide

CV of Michael F. Cuccarese

CV of George A. O'Doherty

References

Chapter 32: Asymmetric C–C Bond Formation Using Chiral Phosphoric Acid

Background

Results

Conclusions and Future Perspectives

CV of Takahiko Akiyama

References

Chapter 33: Asymmetric C–H Bond Functionalization

Background

Results

Conclusions and Future Perspectives

CV of Masayuki Wasa

CV of Kelvin S. L. Chan

CV of Jin-Quan Yu

References

Chapter 34: Asymmetric C–C Bond Formation Using Chiral Guanidine Catalysts

Background

Catalyst Design and Results

CV of Masahiro Terada

References

Chapter 35: Enantioselective Synthesis of Lactones via Rh-Catalyzed Ketone Hydroacylation

Background and Introduction

Strategy and Results

Conclusions and Future Directions

CV of Vy M. Dong

CV of Matthew M. Coulter

References

Chapter 36: Radical Haloalkylation

CV of Armen Zakarian

References

Chapter 37: Asymmetric Hydrovinylation of Alkenes

Introduction

New Protocols for the Heterodimerization of Ethylene/Propylene and Vinylarenes, 1,3-Dienes, and Norbornene

Catalytic Asymmetric Hydrovinylation Reactions: Effects of Hemilabile Ligands

All-Carbon Quaternary Centers via Catalytic Asymmetric HV

Hydrovinylation (HV) of 1,3-Dienes and Asymmetric Variations

Asymmetric Hydrovinylation of Unactivated Linear 1,3-Dienes Using Co(II) Catalysis

Scope and Applications of Hydrovinylation Reactions: Exocyclic Stereocontrol

A Stereoselective Route to either Steroid-C20(S) or -C20(R) Derivatives

Asymmetric Hydrovinylation of Strained Alkenes

Conclusions and Future Perspectives

CV of T. V. (Babu) RajanBabu

References

Chapter 38: Heterocycle Construction via Asymmetric Rhodium-Catalyzed Cycloadditions

Background

Strategy

Results

Application to Other Reactions

Conclusion and Future Perspectives

CV of Tomislav Rovis

CV of Kevin M. Oberg

References

Chapter 39: N-Heterocyclic Carbene-Catalyzed Aldol Desymmetrizations

Introduction

Strategy and Results

Application to the Syntheses of Bakkenolides I, J, and S

Conclusion

CV of Karl A. Scheidt

CV of Eric M. Phillips

CV of Julien Dugal-Tessier

References

Chapter 40: Strategies for the Asymmetric Total Synthesis of Natural Products: “Chiral Pool” versus Chiral Catalysts

Introduction

Catalytic Stereoselective Total Synthesis

Natural Product Synthesis Starting from Chiral, Nonracemic Starting Materials

Conclusion

CV of Karl Gademann

References

Chapter 41: Dynamic Kinetic Asymmetric Transformations Involving Carbon–Carbon Bond Cleavage

Background

Donor–Acceptor Cyclopropanes as DYKAT Substrates

Lewis Acid Catalysis

Palladium Catalysis

Deracemization of Tertiary Propargyl-Allyl Alcohols via Rhodium-Catalyzed Sequential Rearrangement/Enantioselective Conjugate Addition

Conclusion

CV of Andrew Parsons

CV of Jeffrey Johnson

References

Chapter 42: Iron-Catalyzed Allylic Substitutions

Allylic Substitutions Catalyzed by the Hieber-Anion [Fe(CO)3(NO)]−

Allylic Substitutions Catalyzed by Fe2(CO)9

CV of Markus Jegelka

CV of Bernd Plietker

References

Chapter 43: Asymmetric Conia-Ene Carbocyclizations

Introduction and Background: the Conia-ene Reaction

Strategy: Organo/Metal Cooperative Catalysis

Results

CV of Filippo Sladojevich

CV of Darren J. Dixon

References

Chapter 44: Tactics and Strategies in the Total Synthesis of Chlorosulfolipids

Background

Stereoselective Synthesis of vic-Dichloride Fragments

Total Synthesis of Hexachlorosulfolipid

Conclusions

CV of Christian Nilewski

CV of Erick M. Carreira

References

Chapter 45: Linear Free Energy Relationships (LFERs) in Asymmetric Catalysis

Introduction and Background

Hammett Electronic Parameters and Their Application to (salen)Mn(III)-Catalyzed Asymmetric Epoxidation Reactions

Relating Brønsted Acidity to Enantiomeric Ratio in an Asymmetric Hydrogen-Bond-Catalyzed Diels-Alder Reaction

An LFER Describing the Influence of Steric Bulk in a Nozaki–Hiyama–Kishi Asymmetric Allylation of Acetophenone

Correlating Quadrupole Moment to Enantioselectivity in Cation-π-Mediated Asymmetric Polycyclization

Simultaneously Correlating Hammett and Charton Parameters to Enantioselectivity in Two-Dimensional Free Energy Relationships

Conclusions

CV of Elizabeth Bess

CV of Matt Sigman

References

Chapter 46: Asymmetric Diamination of Alkenes

Introduction and Background

Strategy

Results

CV of José Souto

CV of Kilian Muñiz

References

Chapter 47: Enzymatic Asymmetric Synthesis of Tertiary Alcohols

Introduction

YerE–a Unique ThDP-Dependent Enzyme

Hydroxynitrile Lyases

Conclusion

CV of Michael Richter

References

Chapter 48: Oxidative Dearomatization and Organocatalytic Desymmetrization

Introduction

Desymmetrization of Cyclohexadienones

A One-Pot Oxidative Dearomatization and Catalytic Desymmetrization

Oxo- and Aza-Michael Additions

Further One-Pot Methods for Oxidative Dearomatization and Catalytic Desymmetrization

Alkylative Dearomatization

Summary

CV of Matthew J. Gaunt

CV of Alice E. Williamson

References

Chapter 49: Total Synthesis of All (–)-Agelastatin Alkaloids

Introduction

Biosynthetically Inspired Plan for Total Synthesis

Total Synthesis of the Agelastatin Alkaloids

CV of Mohammad Movassaghi

CV of Sunkyu Han

References

Index

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The Editor

Prof. Dr. Mathias Christmann

Technische Universität

Organische Chemie

Otto-Hahn-Str. 6

44227 Dortmund

Germany

Prof. Dr. Stefan Bräse

Institut für Technologie (KIT)

Inst. f. Organische Chemie

Fritz-Haber-Weg 6

76131 Karlsruhe

Germany

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© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

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List of Contributors

Takahiko Akiyama

Gakushuin University

Department of Chemistry

1-5-1 Mejiro

Toshima-ku

Tokyo 171-8588

Japan

Iuliana Atodiresei

Institute of Organic Chemistry

RWTH Aachen University

Landoltweg 1 52074

Aachen

Germany

Phil S. Baran

The Scripps Research Institute

Department of chemistry

10550 N. Torrey Pines Road

San Diego

CA 92037

USA

Santiago Barroso

University of Groningen

Department of Bio Organic Chemistry

Stratingh Institute for Chemistry

Nijenborgh 4

9747 Groningen

The Netherlands

Elizabeth N. Bess

University of Utah

Department of Chemistry

315 S. 1400 E.

Salt Lake City

Utah, 84112-0850

USA

Jeffrey W. Bode

Laboratorium für Organische Chemie

Department of Chemistry and Applied Biosciences

ETH Zürich. Wolfgang Pauli Strasse 10

8093 Zürich

Switzerland

Alexandria P. Brucks

Columbia University

3000 Broadway

New York

NY 10027

USA

Noah Z. Burns

The Scripps Research Institute

Department of chemistry

10550 N. Torrey Pines Road

San Diego

CA 92037

USA

Erick M. Carreira

ETH Zurich

Laboratorium für Organische Chemie

HCI H335

8093 Zürich

Switzerland

Kelvin S. L. Chan

The Scripps Research Institute

Department of Chemistry

10550 N. Torrey Pines Road

La Jolla

CA 92037

USA

Mathias Christmann

Department of Chemistry

Technical University of Dortmund

Otto-Hahn-Str. 6

44227 Dortmund

Germany

Nicolai Cramer

Laboratory of Asymmetric Catalysis and Synthesis

Institute of Chemical Sciences and Engineering

École Polytechnique FÉdÉrale de Lausanne

1015 Lausanne

Switzerland

Matthew M. Coulter

University of Toronto

Department of Chemistry

80 St. George Street

Toronto

ON M5S 3H6

Canada

Michael F. Cuccarese

Northeastern University

Department of Chemistry and Chemical Biology

360 Huntington Ave

Boston

MA 02115

USA

Darren J. Dixon

University of Oxford

Department of Chemistry

Mansfield Road 12

Oxford

OX1 3TA

UK

Vy M. Dong

University of Toronto

Department of Chemistry

80 St. George Street

Toronto

ON M5S 3H6