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Issue 1, 2014
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One-pot formation of fluorescent γ-lactams having an α-phosphorus ylide moiety through three-component α(δ′)-Michael reactions of phosphines with an enyne and N-tosyl aldimines

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Abstract

We demonstrate a straightforward synthesis of γ-lactams possessing an α-phosphorus ylide moiety from assembly of phosphines, N-tosyl aldimines and an enyne through an initial α(δ′)-attack of phosphines to an enyne in up to 79% yield. The investigated multicomponent reaction tolerates a variety of triarylphosphines and electron-poor aldimines to give γ-lactams in one pot. One of the lactams, with the tri(p-tol)phosphine and 4-cyanophenyl moiety, exhibits fluorescence emission at 447 nm with a quantum yield of 0.11.

Graphical abstract: One-pot formation of fluorescent γ-lactams having an α-phosphorus ylide moiety through three-component α(δ′)-Michael reactions of phosphines with an enyne and N-tosyl aldimines

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Publication details

The article was received on 05 Sep 2013, accepted on 15 Oct 2013 and first published on 16 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41811A
Citation: Org. Biomol. Chem., 2014,12, 162-170
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    One-pot formation of fluorescent γ-lactams having an α-phosphorus ylide moiety through three-component α(δ′)-Michael reactions of phosphines with an enyne and N-tosyl aldimines

    Y. Lin, J. Deng, Y. Hsieh and S. Chuang, Org. Biomol. Chem., 2014, 12, 162
    DOI: 10.1039/C3OB41811A

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