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Issue 11, 1995
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Synthesis of azophenolic crown ethers of Cs symmetry incorporating cis-1-phenylcyclohexane-1,2-diol residues as a steric barrier and diastereotopic face selectivity in complexation of amines by their diastereotopic faces

Abstract

Azophenolic crown ethers 1 and 2 of Cs symmetry incorporating cis-1-phenylcyclohexane-1,2-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-dependent 1H 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.

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Article type: Paper
DOI: 10.1039/P19950001429
J. Chem. Soc., Perkin Trans. 1, 1995, 1429-1435

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    Synthesis of azophenolic crown ethers of Cs symmetry incorporating cis-1-phenylcyclohexane-1,2-diol residues as a steric barrier and diastereotopic face selectivity in complexation of amines by their diastereotopic faces

    K. Naemura, S. Takeuchi, M. Asada, K. Ueno, K. Hirose, Y. Tobe, T. Kaneda and Y. Sakata, J. Chem. Soc., Perkin Trans. 1, 1995, 1429
    DOI: 10.1039/P19950001429

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