CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation

INTRODUCTION BASIC CONCEPTS AND NOMENCLATURE OF STEREOCHEMISTRY Chirality, Enantiomers and Diastereomers Stereochemical Nomenclature Principles of Separation of Diastereomers and Enantiomers RESOLUTION BY FORMATION AND FRACTIONAL CRYSTALLISATION OF DIASTEREOMERIC SALTS The Concept of Resolvability Stoichiometry of Resolution Resolution with One Equivalent of Resolving Agent Resolution with Half Equivalent of Resolving Agent in Combination with an Achiral Additive Use of Half Molar Equivalent of Resolving Agent without an Achiral Additive Salt-Salt Resolution Resolution with the Enantiomer of the Resolving Agent Reciprocal Resolution Mutual Resolution Resolution with Difunctional Resolving Agents Resolution of Amphoteric Racemates Resolution by Salt Formation of Compounds Lacking Acidic or Basic Groups Asymmetric Transformations during Resolution by Salt Formation RESOLVING AGENTS Basic Resolving Agents Acidic Resolving Agents (Including Amino Acids) RESEARCH ON RESOLVING AGENTS Attempts to Devise A Generally Applicable Resolving Agent Correlation of the Efficiency of Resolution with the Structure of Racemate and Resolving Agent. Resolutions with a Derivative of the Racemate Resolutions with a Mixture of Structurally Similar Resolving Agents SELECTION OF THE RESOLVING AGENT SELECTION OF THE RESOLVING AGENT BY EXPERIMENTATION Selection of the Resolving Agent by Small-Scale Preliminary Preparative Experiments Selection of the Resolving Agent by Combined Application of Several Resolving Agents Selection of the Resolving Agent by Distillation Tests Selection of the Resolving Agent Based on the Principle of Maximum Similarity Selection of the Resolving Agent by Statistical Evaluation SELECTION OF A RESOLVING AGENT BASED ON THE DETERMINATION OF PHYSICO-CHEMICAL PARAMETERS Solubility Selection of a Resolving Agent Based on Melting Point Phase Diagrams of Diastereomeric Salt Pairs Calculation of Resolvability by DSC of a Mixture of Diastereomeric Salts Formed from the Racemate Determination of the Optical Rotation of Diastereomeric salts SELECTION OF THE RESOLVING AGENT BASED ON THEORETICAL CONSIDERATIONS RESOLUTION IN PRACTICE, SELECTION OF THE OPTIMAL PARAMETERS Reacting the Components Initiation of Crystallisation Role of Temperature in Resolution Further Purification of Diastereomeric Salts with the Aid of a Chiral Additive Recovery of the Components from the Diastereomeric Salts Upgrading of Optical Purity without a Chiral Additive (Enantiomeric Enrichment) ALTERNATIVE METHODS OF RESOLUTION BY DIASTEREOMERIC SALT FORMATION Classification of Alternative Resolution Processes by Type of Phase Transition Resolution by Distillation Resolution by Extraction Resolution by Supercritical Extraction Resolution by Sublimation Mechanical Separation of Diastereomeric Salt Mixtures DETAILED DESCRIPTIONS OF SELECTED RESOLUTIONS APPENDIX 1: Resolutions Ordered According to the Resolving Agent APPENDIX 2: Commercially Produced Resolving Agents and Optically Active Industrial Products which may be Eligible as Resolving Agents APPENDIX 3. Chiral Selective Chromatographic Analysis