Different Strategies for Obtaining Enantiopure Hemicryptophanes

Abstract

Hemicryptophanes have recently emerged as an attractive class of cages due to their interesting applications as supramolecular receptors and catalysts. Over the last decade, substantial advances have been made regarding the preparation of enantiopure versions of these synthetic receptors. Enantiopure hemicryptophanes are commonly obtained through the separation of diastereomers by chromatography, or by resolution of racemic mixtures using chiral HPLC. This short review summarizes the existing methods to access to these chiral organic architectures and discusses the benefits and drawbacks of each approach.

1 Introduction

2 Enantiopure Hemicryptophanes Obtained by Introducing Additional Chiral Units and Separation of Diastereomers

2.1 Synthesis by Means of Intramolecular Macrocyclization Reactions

2.2 [1+1] Coupling of the CTV and the Southern Part

3 Enantiopure Hemicryptophanes Obtained by Means of Chiral HPLC Resolution of Enantiomers

3.1 Resolution of Hemicryptophane Racemates

3.2 Resolution of CTV-Based Precursor Racemates

4 Conclusion

Key words

hemicryptophanes - chiral recognition - resolution - cyclotriveratrylene - supramolecular chemistry

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