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Issue 47, 2015
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Cu(II)-catalyzed enantioselective oxygen atom transfer from oxaziridine to oxindole derivatives with chiral phenanthroline

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Abstract

In the presence of a Cu(II) complex of axially chiral, N,N,O-tridentate phenanthroline ligand (S)-2, asymmetric oxygen atom transfer of oxindole derivatives (3) using Davis’ oxaziridine (4) occurred to give the corresponding 3-aryl-3-hydroxy-2-oxindole derivatives (1) with excellent enantioselectivity (up to 96% ee). The X-ray crystallographic analysis of the isolated Cu(II) complex disclosed its N,N,O-tridentate coordination, which is critical to realize effective catalytic activity.

Graphical abstract: Cu(ii)-catalyzed enantioselective oxygen atom transfer from oxaziridine to oxindole derivatives with chiral phenanthroline

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Publication details

The article was received on 03 Sep 2015, accepted on 28 Sep 2015 and first published on 02 Oct 2015


Article type: Paper
DOI: 10.1039/C5OB01840D
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 11499-11506
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    Cu(II)-catalyzed enantioselective oxygen atom transfer from oxaziridine to oxindole derivatives with chiral phenanthroline

    Y. Naganawa, T. Aoyama and H. Nishiyama, Org. Biomol. Chem., 2015, 13, 11499
    DOI: 10.1039/C5OB01840D

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