Synthesis and stereochemical configuration of inherently chiral p-tert-butylcalix[4]arene carboxylic acids and their derivatives

Both enantiomers of inherently chiral p - tert -butylcalix[4]arene carboxylic acids with ABHH substitution patterns have been prepared by stereoselective reaction of monopropoxy- p - tert -butylcalix[4]arene with an ( R )- N -(1-phenylethyl)bromoacetamide, separation of the diastereomers by column c...

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Bibliographic Details
Published inJournal of inclusion phenomena and macrocyclic chemistry Vol. 77; no. 1-4; pp. 175 - 181
Main Authors Karpus, Andrii O., Yesypenko, Oleksandr A., Andronov, Leonid P., Boyko, Vyacheslav I., Voitenko, Zoia V., Chernega, Alexander N., Kalchenko, Vitaly I.
Format Journal Article
LanguageEnglish
Published Dordrecht Springer Netherlands 01.12.2013
Subjects
Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Food Science
Organic Chemistry
Original Article
Butylcalixarene carboxylic acid
Enantiomers
-
Inherently chiral calixarenes
Absolute configuration
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Summary:Both enantiomers of inherently chiral p - tert -butylcalix[4]arene carboxylic acids with ABHH substitution patterns have been prepared by stereoselective reaction of monopropoxy- p - tert -butylcalix[4]arene with an ( R )- N -(1-phenylethyl)bromoacetamide, separation of the diastereomers by column chromatography, and removal of the chiral auxiliary groups. The absolute configuration of obtained compounds has been established by X-ray analysis. Graphical Abstract
ISSN:1388-3127
1573-1111
DOI:10.1007/s10847-012-0231-8