Calix[4]arenes with Combined Axial Chirality and Inherent Chirality: Synthesis, Absolute Configuration and Chiral Recognition

Wen Zhen Zhang, Hui Ma, Guang Ya Xiang, Jun Luo*, Wen-Sheng Chung

*Corresponding author for this work

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Calix[4]arene diastereomeric pairs with combined axial chirality and inherent chirality were readily synthesized via monoalkylation of 1,2-substituted calix[4]arene crown-4 incorporating an axially chiral binaphthyl moiety with different electrophiles as a key step. The reaction showed high generality and distinct diastereoselectivity. The easy separation of the diastereomers, the good diastereoselectivity of the reaction, and the poor stereoselectivity of the chiral recognition of diastereomeric pairs were attributed to the remarkable steric effect of the axially chiral binaphthyl moiety. Absolute configurations were determined by X-ray crystallography.

Original languageEnglish
Pages (from-to)2486-2491
Number of pages6
JournalChemistrySelect
Volume1
Issue number10
DOIs
StatePublished - 1 Jan 2016

Keywords

  • Calixarenes
  • Chirality
  • Diastereoselectivity
  • Molecular recognition
  • Supramolecular chemistry

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