A rational synthesis of trans-2-(3-phenylprop-1-yl)cyclohexylamino-2-oxazoline enantiomers

A novel method has been developed for the synthesis of the optical antipodes of trans-2-(3-phenylprop-1-yl)cyclohexylamino-2-oxazoline 1 from racemic cis-octahydrocoumarin 4 instead of cyclohexene oxide 2, because the synthesis of 1 from compound 2 was unsuccessful. Compound 4 was resolved with 1-ph...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 19; no. 7; pp. 773 - 778
Main Authors Schindler, József, Faigl, Ferenc, Hegedűs, László, Pálovics, Emese, Fogassy, Elemér
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.04.2008
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
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Summary:A novel method has been developed for the synthesis of the optical antipodes of trans-2-(3-phenylprop-1-yl)cyclohexylamino-2-oxazoline 1 from racemic cis-octahydrocoumarin 4 instead of cyclohexene oxide 2, because the synthesis of 1 from compound 2 was unsuccessful. Compound 4 was resolved with 1-phenylethylamine enantiomers. Although the preparation of this oxazoline from cyclohexene oxide is known, the resolution and the enantiomeric enrichment step have not been described.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2008.02.029