Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis

Filling the gap in the literature, this book presents everything there is to know about this topic. By comprehensively covering the quaternary stereocenters found in a range of important and useful molecules in pharmaceutical and medicinal applications, as well as in thousands of natural products, the book provides the know-how chemists need to synthesize challenging molecules with numerous applications. A must for organic chemists in academia, the pharmaceutical industry and medicine. From the Contents: Important Natural Products Important Pharmaceuticals and Intermediates Aldol Reactions Michael Reactions and Conjugate Additions Cycloaddition Reactions Rearrangement Reactions Alkylation of Ketones and Imines Asymmetric Allylic Alkylation Asymmetric Cross Coupling and Heck Reactions Phase Transfer Catalysis Enzymatic Methods Radical Reactions

Table of Contents:
Foreward. Preface. List of Contributors. Symbols and Abbreviations. 1 Important Natural Products (Hirokazu Arimoto and Daisuke Uemura). 1.1 Introduction. 1.2 Alkylation of Tertiary Carbon Centers. 1.3 Cycloaddition to Alkenes. 1.4 Rearrangement Reactions. 1.5 Carbometallation Reactions. 1.6 C-H Functionalization Reactions. 1.7 Asymmetric Modification of Enantiotopic/Diastereotopic Substituents of Quaternary Carbon Centers. 1.8 Summary. 2 Important Pharmaceuticals and Intermediates (Johannes G. de Vries). 2.1 The Chirality of Drugs and Agrochemicals. 2.2 Steroids. 2.3 Pharmaceuticals and Agrochemicals Based on a-Dialkylated Amino Acids. 2.4 Azole Antimycotics. 2.5 Alkaloids. 2.6 HIV Inhibitors. 2.7 β-Lactam Antibiotics. 2.8 The Tetracyclines. 2.9 Summary and Outlook. 3 Aldol Reactions (Bernd Schetter and Rainer Mahrwald). 3.1 Introduction. 3.2 Metal Enolates. 3.3 Catalytic Aldol Additions. 3.4 Conclusions. 3.5 Note Added in Proof 79 4 Michael Reactions and Conjugate Additions (Angelika Baro and Jens Christoffers). 4.1 Introduction. 4.2 Chiral Bronstedt Bases. 4.3 Chiral Metal Complexes. 4.4 Chiral Auxiliaries. 5 Rearrangement Reactions (Annett Pollex and Martin Hiersemann). 5.1 Introduction. 5.2 Applications. 5.3 Summary. 6 Cycloaddition Reactions (Giovanni Desimoni and Givseppe Faita). 6.1 Introduction. 6.2 [2+1] Cycloaddition Reactions. 6.3 [2+2] Cycloaddition Reactions. 6.4 1,3-Dipolar Cycloaddition Reactions. 6.5 Diels-Alder Reactions. 6.6 Hetero-Diels-Alder Reactions. 6.7 Consecutive Cycloaddition Reactions. 7 Asymmetric Cross-coupling and Mizoroki-Heck Reactions (Louis Barriault and Effiette L. O. Sauer). 7.1 The Asymmetric Heck Reaction. 7.2 Metal-catalyzed Cross-coupling Reactions. 7.3 Summary. 8 Alkylation of Ketones and Imines (Diego J. Ramon and Miguel Yus). 8.1 Introduction. 8.2 Diastereoselective Additions. 8.3 Enantioselective Additions by Modulated Processes. 8.4 Enantioselective Additions by Promoted Processes. 9 Asymmetric Allylic Alkylation (Manfred Braun). 9.1 Introduction. 9.2 Electrophilic Allylic Alkylation. 9.3 Nucleophilic Allylic Alkylation. 9.4 Miscellaneous Methods. 9.5 Outlook. 10 Phase-Transfer Catalysis (Takashi Ooi and Keiji Maruoka). 10.1 Introduction. 10.2 Carbon-Carbon Bond Formation Through PTC. 10.3 Carbon-Heteroatom Bond Formation Through PTC. 10.4 Conclusion. 11 Radical Reactions (Kalyani Patil and Mukund P. Sibi). 11.1 Introduction. 11.2 Radical Cyclization. 11.3 Atom- and Group-transfer Cyclizations. 11.4 Intermolecular Radical Allylations. 11.5 Other Metallic Reagents. 11.6 Radical Reactions in the Solid State. 11.7 Conclusion. 11.8 Experimental. 12 Enzymatic Methods (Uwe T. Bornscheuer, Erik Henke, and Jurgen Pleiss). 12.1 Introduction. 12.2 Strategies for the Kinetic Resolution of Sterically Demanding Substrates. 12.3 Conclusion. Index.

About the Author :
Born in Germany in 1966, Jens Christoffers received his diploma from the University of Marburg, Germany in 1992, before moving to Bonn, Germany, where he completed his doctorate in 1994 on Fischer carbene complexes and Pauson-Khand reactions. He became involved with zirconocene catalysis during a post doctorate under Professor R. G. Bergman in Berkeley, USA, and in 1996 started his independent career at the Technical University Berlin, Germany, gaining his lecturing qualification under Professor S. Blechert in 2000. He has been Professor of Organic Chemistry at the University of Stuttgart, Germany, since 2001. Professor Christoffers's current research interests are in the fields of asymmetric catalysis, synthesis of heterocyclic compounds and catalytic oxidation reactions utilizing molecular oxygen. Angelika Baro studied chemistry at the Georg-August-Universitat Gottingen, Germany, where she received her PhD degree in Clinical Biochemistry in 1987 under the supervision of Professor H. D. Soling. Since 1991 she has been a scientific staff member at the Institute for Organic Chemistry at the University of Stuttgart.

Review :
"This book is clearly timely and fills an important niche. The chemical practitioner will find it an excellent resource...it also is a useful beginning point for students..." (Journal of the American Chemical Society, June 21, 2006) "This text should be welcomed by anyone involved in the practice or teaching of organic synthesis..." (Journal of Medicinal Chemistry, April 20, 2006) "...a handsome little book...I expect it to become a must for anyone who has any pretensions to the practice of organic synthesis..." (Chemistry World, 1st February 2006) "I am...looking forward to having this...reference guide for all new students in our laboratory." (Journal Of Medical Chemistry 2006, Vol 49 No.8)