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Towards a rational design of resolving agents. Part II: Correlation between resolution results and physical properties of diastereomeric salts

✍ Scribed by A. D. van der Haest; H. Wynberg; F. J. J. Leusen; A. Bruggink

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 525 KB
Volume: 109
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19901091007

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✦ Synopsis

Abstract

Six closely related cyclic phosphoric acids (1a‐f) were compared with respect to their resolving ability towards ephedrine. Variation of the aromatic substituent in the phosphoric acids significantly influences this ability. Studying the results of the resolution experiments as a function of some physico‐chemical properties of the diastereomeric salts reveals a relationship between the resolving ability of a particular phosphoric acid and the difference in heat of fusion of its diastereomeric salts.

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## Abstract Detailed structural studies of five pairs of diastereomeric salts of ephedrine and halogen‐substituted chiral cyclic phosphoric acids indicate a correlation between the efficiency of the resolution process and the lattice energy difference between the salts of a diastereomeric pair. Att