Asymmetric Synthesis : The Essentials

by Editor: Mathias Christmann (Institute of Organic Chemistry, RWTH Aachen, Aachen, Germany); Editor: Stefan Bräse (Institute of Organic Chemistry, University of Karlsruhe, Germany)

• ISBN13: 9783527313990
• ISBN10: 3527313990
• Edition: 1st
• Format: Paperback
• Copyright: 2007-02-01
• Publisher: Wiley-VCH

Summary

A veritable "Who's who" of asymmetric synthesis introduces the reader to the leaders in the field with a four-page concentrate of their area of research along with a short biography. The book is organized into five chapters, each with an introductory preface. Starting from the key concepts of asymmetric synthesis diastereoselective methods, asymmetric catalysis) the Focus then shifts to its application to the synthesis natural products and industrial processes. Graduate students, academic and industrial researchers will find this book a rich source of inspiration for their own work as well as an indispensable tool for the preparation of seminars and exams. A must for everyone in the field.

Author Biography

Mathias Christmann is currently working as assistant professor at the university of Aachen.

Stefan Braese is a young and successful researcher, working at the University of Karlsruhe. He has published nearly 100 publications and is recipient of the ORCHEM award in 2000.

Table of Contents

Foreword.

Message from the editors.

List of Abbreviations.

Named and Unnamed Reactions.

List of Contributors.

Part I.

Chiral Auxiliaries in Asymmetric Synthesis (David A. Evans, Günter Helmchen and Magnus Rüping).

Asymmetric Epoxidation of Pentadienols (Reinhard Brückner).

Asymmetric Synthesis using Sulfur–Nitrogen Reagents (Franklin A. Davis).

Asymmetric Syntheses with SAMP-/RAMP-Hydrazones (Dieter Enders and Wolfgang Bettray).

Asymmetric Allylation Reactions (Reinhard W. Hoffmann).

Carbohydrates as Chiral Auxiliaries (Horst Kunz).

The Use of Chiral Oxazolines in early C–C Bond Forming Reactions (Albert I. Meyers).

Asymmetric Synthesis of Amines and Amino Acids from Amines (Shun-Ichi Murahashi and Yasushi Imada).

Part II.

Metal-catalyzed Asymmetric Synthesis (Masakatsu Shibasaki and Shigeki Matsunaga).

Catalytic Asymmetric Sulfur Ylide Mediated Epoxidation of Carbonyl Compounds (Varinder Aggarwal).

Asymmetric Baeyer-Villiger Reactions (Carsten Bolm).

Planar Chiral Ligands Based on [2.2]Paracyclophanes (Stefan Brse).

Asymmetric Syntheses of 3-(trans-2-Nitrocyclopropyl)alanine and 3-(trans-2-Aminocyclopropyl)alanine (Armin de Meijere and Oleg V. Larionov).

Copper-Bis(oxazoline) Catalyzed Synthesis of βs – Enantioselective Reaction of Alkynes with Nitrones (David A. Evans, Florian Kleinbeck and Magnus Rüping).

Catalytic Asymmetric Conjugate Addition Reactions of Organometallic Reagents (Fernando López and Ben L. Feringa).

Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution (Hans-Joachim Gais).

Asymmetric Cross-Coupling Reactions (Tamio Hayashi).

Asymmetric Allylic Substitutions (Günter Helmchen).

Asymmetric Homoaldol Reactions (Dieter Hoppe).

Asymmetric Vinylogous Mukaiyama Aldol Reaction (Markus Kalesse and Jorma Hassfeld).

Chiral Lewis Acid Catalysis in Aqueous Media (Sh Kobayashi and Chikako Ogawa).

Asymmetric Epoxidation of Non-activated Olefins (Kazuhiro Matsumoto and Tsutomu Katsuki).

Chiral Carbonyl Lewis Acid Complexes in Asymmetric Syntheses (Keiji Maruoka and Takashi Ooi).

ZACA Reaction: Zr-Catalyzed Asymmetric Carboalumination of Alkenes (Ei-ichi Negishi, Bo Liang, Tibor Novak, and Ze Tan)

Bisoxazolines – a Privileged Ligand Class for Asymmetric Catalysis (Andreas Pfaltz).

Enantioselective Cycloaddition Reactions Catalyzed by Hydrogen Bonding (Viresh H. Rawal and Avinash N. Thadani).

Direct Catalytic Asymmetric Aldol-Tishchenko Reaction (Masakatsu Shibasaki and Takashi Ohshima).

Asymmetric Heck and other Palladium-catalyzed Reactions (Lutz F. Tietze and Florian Lotz).

Asymmetric Catalysis with Chiral Acid (Hisashi Yamamoto).

Part III.

Biocatalysis and Organocatalysis: Asymmetric Synthesis Inspired by Nature (Benjamin List).

Enantioselective Photochemical Reactions (Thorsten Bach).

Asymmetric Catalysis via Dynamic Kinetic Resolution (Jan-E. Bckvall).

Catalytic Asymmetric Epoxidation of Enones and Related Compounds (Albrecht Berkessel).

Kinetic Investigations of the Soai Autocatalytic Reaction (Donna G. Blackmond).

Planar-chiral Heterocycles as Enantioselective Organocatalysts (Gregory Fu).

An Organocatalytic Approach to Optically Active Six-membered Rings (Karl Anker Jørgensen).

Non-linear Effects in Asymmetric Catalysis (Henri B. Kagan).

Asymmetric Organocatalysis (Steven V. Ley).

Directed Evolution of Enzymes for Asymmetric Syntheses (Manfred T. Reetz).

Asymmetric Autocatalysis and Its Implications in the Origin of Chiral Homogeneity of Biomolecules (Kenso Soai and Tsuneomi Kawasaki).

Asymmetric Synthesis using Deoxyribose-5-phosphate Aldolase (Chi-Huey Wong and William A. Greenberg).

Part IV.

Asymmetric Reactions in Total Synthesis (K. C. Nicolaou and Paul G. Bulger).

Ring Rearrangement Metathesis (RRM) in Alkaloid Synthesis (Nicole Holub and Siegfried Blechert).

Asymmetric Synthesis of Biaryls by the ‘Lactone Method’ (Gerhard Bringmann, Tanja Gulder, and Tobias A. M. Gulder).

Asymmetric Synthesis of Merrilactone A (Samuel J. Danishefsky).

Asymmetric Synthesis of Cyclic Ketal and Spiroaminal-Containing Natural Products (Craig J. Forsyth).

Case Studies at the Metathesis/Asymmetric Synthesis Interface (Alois Fürstner).

Asymmetric Synthesis of Amino Acids by Rhodium and Ruthenium Catalysis (Jean Pierre Genet).

Asymmetric Syntheses of Pheromones (Kenji Mori).

Total Synthesis of Polyketides Using Asymmetric Aldol Reactions (Ian Paterson).

Asymmetric Synthesis on the Solid Phase (Torben Leßmann and Herbert Waldmann).

Part V.

Asymmetric Synthesis in Industry (Herbert Hugl).

Industrial Application of Enantioselective Catalysis (Hans-Ulrich Blaser).

Crystallization-Induced Diastereoselection for the Synthesis of Aprepitant (Karel M. Jos Brands, Philip Pye and Kai Rossen).

Combinatorial Methods in Asymmetric Syntheses (Stefan Dahmen).

Biocatalytic Production of Optically Active Amines (Klaus Ditrich).

The Monsanto L-Dopa Process (William S. Knowles).

Asymmetric Hydrogenation through Metal–Ligand Bifunctional Catalysis (Ryoji Noyori, Takeshi Ohkuma, Christian A. Sandoval, and Kilian Muñiz).

Many Ways are Leading to Rome – Today’s Variety of Competing Synthetic Methods in Industry (Andreas Job and Andreas Stolle).

Index.

Author Index.

Subject Index.

Related Titles.