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Issue 24, 2017
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Stereoselective synthesis of enamino ketones through an aza-Michael/hydrolysis cascade reaction

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Abstract

We have developed a mild, convenient and efficient synthesis of highly functionalized (Z)-β-enamino ketones from readily available 3,4-dihydroisoquinoline imines and ynones through an aza-Michael/hydrolysis cascade reaction. This method is also suitable for the preparation of (Z)-β-enamino esters using alkynoates as starting materials. Complex fully substituted pyrroles can be constructed from the obtained (Z)-β-enamino ketones. It is an attractive alternative approach for the preparation of highly functionalized enamino ketones, esters and pyrroles.

Graphical abstract: Stereoselective synthesis of enamino ketones through an aza-Michael/hydrolysis cascade reaction

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Publication details

The article was received on 28 Apr 2017, accepted on 23 May 2017 and first published on 25 May 2017


Article type: Communication
DOI: 10.1039/C7OB01032J
Citation: Org. Biomol. Chem., 2017,15, 5121-5125
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    Stereoselective synthesis of enamino ketones through an aza-Michael/hydrolysis cascade reaction

    H. Cui, L. Peng, H. Zhou, X. You and X. Jiang, Org. Biomol. Chem., 2017, 15, 5121
    DOI: 10.1039/C7OB01032J

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