Synthesis of azophenolic crown ethers of Cs symmetry incorporating cis-l-phenylcyclohexane-l,2-cliol residues as a steric barrier and diastereotopic face selectivity in complexation of amines by their diastereotopic faces

Koichiro Naemura*, Sachiko Takeuchi, Masaki Asada, Koji Ueno, Keiji Hirose, Yoshito Tobe, Takahiro Kaneda, Yoshiteru Sakata

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

Azophenolic crown ethers 1 and 2 of Cs symmetry incorporating cw-l-phenylcyclohexane-l,2-diol residues as a steric barrier have been prepared. Diastereotopic face selectivity in complexation with 2-methoxyethylamine, n-propylamine and ethanolamine was examined using temperature-dependent1H NMR spectroscopy. Both bind ethanolamine stereoselectively to one of their diastereotopic faces; the prediction of which diastereoisomeric complex was preferentially formed is made on the basis of a CPK molecular-model examination of the complexes.

Original languageEnglish
Pages (from-to)1429-1435
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
StatePublished - 1 Jan 1995

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