Helvetica Chimica Acta p. 1622 - 1635 (1991)
Update date:2022-07-29
Topics: Temperature Dependence Glycine β-Alanine
Kinkel, Joachim N.
Gysel, Urs
Blaser, Denis
Seebach, Dieter
Chiraspher, a polymer of ethyl N-acryloylphenylalanine on spherical silica gel, is used for the preparative separation by recycling chromatography of the enantiomers of oxazolidinones rac-5, thioxolanone rac-6, perhydropyrimidinone rac-7, and dioxinones rac-9 and 10 derived from the acids listed in the title (Figs. 1-5).The oxazolidinones rac-1a, -2, and -4 show a peculiar peak of the separation efficiences upon lowering the Chiraspher-column temperature to 15 deg C (Fig.6).In some cases, multigram amounts of enantiomerically pure heterocycles could thus be prepared.The absolute configuration of most enantiomers are assigned.First application of the tert-butyl 5-oxo-2-phenyloxazolidine-3-carboxylate (5) as a nucleophilic chiral glycine building block are described (products 13-16, Scheme 2).A list of enantiomerically pure 1,3-dioxinones is presented (Table 1), showing a correlation between their absolute configuration, sense of optical rotation, and elution behavior on Chiraspher.
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