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Issue 19, 2001
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Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

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Abstract

Selective formation of (E)-α,β-unsaturated amides by intermolecular three-component reaction between aldehydes, amines (1° or 2°) and ketenylidenetriphenylphosphorane (Ph3P[double bond, length as m-dash]C[double bond, length as m-dash]C[double bond, length as m-dash]O) is described. Natural amides such as fagaramide and piperines could be prepared from immediately available educts. The method is shown to be extendable to the preparation of thioesters from thiols and aldehydes.

Graphical abstract: Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

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Publication details

The article was received on 27 Jun 2001, accepted on 10 Aug 2001 and first published on 12 Sep 2001


Article type: Paper
DOI: 10.1039/B105745F
Citation: J. Chem. Soc., Perkin Trans. 1, 2001,0, 2393-2397

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    Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

    R. Schobert, S. Siegfried and G. J. Gordon, J. Chem. Soc., Perkin Trans. 1, 2001, 0, 2393
    DOI: 10.1039/B105745F

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