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Issue 60, 2013
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Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction

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Abstract

A palladium-catalyzed hydroamination reaction is the key step in a stereoselective synthesis of 2,5-disubstituted and 2,3,5-trisubsituted morpholines from carbamate-protected aziridines. Aziridines are selectively attacked at the more substituted position by unsaturated alcohol nucleophiles using Lewis acid catalysts. Palladium-catalyzed hydroamination of the resulting aminoalkenes gives morpholines as a single diastereomer in excellent yield.

Graphical abstract: Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction

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Publication details

The article was received on 31 May 2013, accepted on 12 Jun 2013 and first published on 13 Jun 2013


Article type: Communication
DOI: 10.1039/C3CC44117B
Citation: Chem. Commun., 2013,49, 6800-6802
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    Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction

    A. McGhee, B. M. Cochran, T. A. Stenmark and F. E. Michael, Chem. Commun., 2013, 49, 6800
    DOI: 10.1039/C3CC44117B

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