Design of Resolving Agents Based on Crystal Engineering

Abstract

As a result of systematic studies on the optical resolution of racemates via crystallization, we have found that in many cases, common characteristic hydrogen-bond networks were formed in the less-soluble diastereomeric salts or conglomerates. Design of resolving/derivatizing agents could be achieved on the basis of the concept of crystal engineering, by which molecules were designed to achieve stable hydrogen-bond networks with target racemates.

• 1 Introduction

• 2 Design of Acidic Resolving Agents for Diastereomeric ­Resolution

• 2.1 Systematic Study of the Resolution of 1-Arylethylamines with Mandelic Acid

• 2.2 p-Substituted Mandelic Acids

• 2.3 2-Naphthylglycolic Acid

• 3 Design of Basic Resolving Agents for Diastereomeric ­Resolution

• 3.1 Systematic Study of the Resolution of 2-Arylalkanoic Acids with 2-Amino-1,2-diphenylethanol

• 3.2 cis-1-Aminoindan-2-ol

• 3.3 trans-1-Aminoindan-2-ol, trans-Aminoindan-1-ol, and trans-Aminoindan-3-ol

• 4 Design of Spontaneous Resolutions

• 4.1 Salts of Achiral Carboxylic Acids with Racemic Primary Amines

• 4.2 Salts of Racemic Acids with Racemic Primary Amines

• 5 Summary

Key words

chiral resolution - chirality - enantiomeric resolution - supramolecular chemistry

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