In one handy volume this handbook summarizes the most common synthetic methods for the separation of racemic mixtures, allowing an easy comparison of the different strategies described in the literature.
Alongside classical methods, the authors also consider kinetic resolutions, dynamic kinetic resolutions, divergent reactions of a racemic mixture, and a number of "neglected" cases not covered elsewhere, such as the use of circularly polarized light, polymerizations, "ripening" processes, dynamic combinatorial chemistry, and several thermodynamic processes.
The result is a thorough introduction to the field plus a long-needed, up-to-date overview of the chemical, biological, and physical methods and their applications. Newcomers to the field, students as well as experienced synthetic chemists will benefit from the highly didactic presentation: Every method is presented in detail, from relatively simple separation problems to advanced complex resolution methods.
An Associate Professor at The University of Sydney's School of Chemistry, Matthew Todd gained his BA and PhD from Cambridge University, UK, where he later became a Fellow in Chemistry. Prior to taking up his current position, he was a Wellcome Trust postdoctoral fellow at the University of California, Berkeley, USA, from 1999 to 2000, and then became a lecturer in organic chemistry at the Department of Chemistry, Queen Mary, University of London from 2001 to 2005. Prof. Todd's research group is investigating synthetic methodology, responsive metal complexes, and asymmetric catalysis. He has received awards for his work in open science, most notably his creation of the Open Source Malaria consortium that is trialling a new model of drug discovery.
INTRODUCTION: A SURVEY OF HOW AND WHY TO SEPARATE ENANTIOMERS Classical Methods Kinetic Resolution ('KR') Dynamic Kinetic Resolution ('DKR') Divergent Reactions of a Racemic Mixture ('DRRM') Other Methods STOICHIOMETRIC KINETIC RESOLUTION REACTIONS Introduction Kinetic Treatment Chiral Reagents and Racemic Substrates Enantiodivergent Formation of Chiral Product Enantioconvergent Reactions Diastereomer Kinetic Resolution Some Applications of Kinetic Resolution Conclusion CATALYTIC KINETIC RESOLUTION Introduction Kinetic Resolution of Alcohols Kinetic Resolution of Epoxides Kinetic Resolution of Amines Kinetic Resolution of Alkenes Kinetic Resolution of Carbonyl Derivatives Kinetic Resolution of Sulfur Compounds Kinetic Resolution of Ferrocenes Conclusions APPLICATION OF ENZYMES IN KINETIC RESOLUTIONS, DYNAMIC KINETIC RESOLUTIONS AND DERACEMIZATION REACTIONS Introduction Kinetic Resolutions Using Hydrolytic Enzymes Dynamic Kinetic Resolution Deracemization Enantioconvergent Reactions Conclusions DYNAMIC KINETIC RESOLUTION (DKR) Introduction Definition and Classification Dynamic Kinetic Resolution (DKR) Mathematical Expression DKR-Related Methods Concluding Remarks ENANTIODIVERGENT REACTIONS: DIVERGENT REACTIONS ON A RACEMIC MIXTURE AND PARALLEL KINETIC RESOLUTION Introduction: The Conceptual Basis for Kinetic Resolution and Enantiodivergent Reactions Divergent RRM Using a Single Chiral Reagent: Ketone Reduction Divergent RRM under Oxidative Conditions Organometallic Reactions and Regiodivergent RRM Regiodivergent RRM in Selective Reactions of Difunctional Substrates Divergent RRM Using Two Chiral Reagents: Parallel Kinetic Resolution (PKR) Conclusion RARE, NEGLECTED AND POTENTIAL SYNTHETIC METHODS FOR THE SEPARATION OF ENANTIOMERS Resolution through the Selfish Growth of Polymers: Stereoselective Polymerization Resolution through Photochemical Methods Combinations of Crystallization and Racemization Destruction then Recreation of Stereocentres: Enantioselective Protonations Dynamic Combinatorial Chemistry Asymmetric Autocatalysis Miscellaneous Concluding Remarks Index