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

  • Andrii O. Karpus
  • Oleksandr A. Yesypenko
  • Leonid P. Andronov
  • Vyacheslav I. BoykoEmail author
  • Zoia V. Voitenko
  • Alexander N. Chernega
  • Vitaly I. Kalchenko
Original Article

Abstract

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

Keywords

p-tert-Butylcalix[4]arene carboxylic acid Inherently chiral calixarenes Enantiomers Absolute configuration 

Notes

Acknowledgments

This work was partially supported by the State Fund for Fundamental Research of Ukraine.

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Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Andrii O. Karpus
    • 1
    • 2
  • Oleksandr A. Yesypenko
    • 1
  • Leonid P. Andronov
    • 1
  • Vyacheslav I. Boyko
    • 1
    Email author
  • Zoia V. Voitenko
    • 2
  • Alexander N. Chernega
    • 1
  • Vitaly I. Kalchenko
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKyiv-94Ukraine
  2. 2.Department of ChemistryKiev National Taras Shevchenko UniversityKyivUkraine

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