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

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...

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Veröffentlicht in:	Organic & biomolecular chemistry 2014-01, Vol.12 (1), p.162-170
Hauptverfasser:	Lin, Yu-Wei, Deng, Jie-Cheng, Hsieh, You-Zung, Chuang, Shih-Ching
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Sprache:	eng
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container_title	Organic & biomolecular chemistry
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creator	Lin, Yu-Wei Deng, Jie-Cheng Hsieh, You-Zung Chuang, Shih-Ching
description	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.
doi_str_mv	10.1039/c3ob41811a
format	Article
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title	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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