CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation: 1st Edition (Hardback) book cover

CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation

1st Edition

Edited by David Kozma

CRC Press

704 pages

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Hardback: 9780849300196
pub: 2001-10-18
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pub: 2001-10-18
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Description

Optically active compounds are gaining ever-increasing importance in organic chemistry, both in the academic and the industrial arenas. The rational synthesis of the growing number of chiral chemicals, drugs, and natural products demands efficient methods for producing these compounds in an enantiomerically, highly pure form. Despite the available alternative techniques, optical resolution via Diastereomeric salt formation remains the most widely used method of preparing pure enantiomers.

The CRC Handbook of Optical Resolutions Via Diastereomeric Salt Formation is the first book to exclusively address this important organic chemical process. It provides fast, one-stop access to a wealth of information, including all of the available data on 100 resolving agents, a list of 500 optically active compounds available in bulk along with their suppliers, data on more than 3,500 resolutions, and 4,200 citations.

This handbook helps answer virtually any question that may arise during the development of a new resolution process.

Which resolving agent and solvent should I use under these conditions?

How can I separate the diastereoisomers?

How can I optimize a resolution process?

How do I determine enantiomeric purity?

Which supplier has the resolving agent I need?

For a racemate already resolved, what were the resolving agent, solvent, and relevant citation?

This is the first book to deal exclusively with all aspects of this important organic chemical process, both theoretical and practical. With an abundance of analyzed examples, this single, authoritative reference provides all of the information you need to perform, develop, and optimize optical resolutions via Diastereomeric salt formation

Reviews

"…a comprehensive survey of the most widely used methods of obtaining pure enantiomers…a wealth of information on all aspects of the optical resolution of racemates by diastereomeric salt formation, including priniciples of resolvability, mechanisms, and kinetics, very valuable lists of commonly used resolving agents, and of optically active commercially produced agents…and summaries of 4000 resolutions by diastereomeric salt formation, which are invaluable in resolving an unknown racemate…well organized to facilitate fast access to the information and data…The handbook will be useful for researchers, engineers, and graduates…affordable for many research libraries, laboratories, and personal collections."

- Svetlana Korlev, University of Wisconsin, Golda Meir Library, USA in E-Streams, vol. 5 no. 8

Table of Contents

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

Subject Categories

BISAC Subject Codes/Headings:
SCI013040
SCIENCE / Chemistry / Organic
SCI013050
SCIENCE / Chemistry / Physical & Theoretical