Isopropylidene glycerol hydrogen phthalate as a resolving agent: a study of its diastereomeric salts with (S)- and (R)-1-phenylethylamine

An insight into the mechanism of the highly efficient resolution of I-pheny lethylamine with enantiomerically pure isopropylideneglycerol hydrogen phth alate is provided by comparison of physicochemical and X-ray crystallograph ic data of the two diastereomeric salts formed by the amine with the S acid , Tn the nearly identical structures of these salts, the different disposit ion of the isopropylidene glycerol moiety stands out drawing attention to t he critical role played by the chiral part of the acid in the discriminatio n between the amine enantiomers. (C) 2000 Elsevier Science Ltd. All rights reserved.