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Issue 12, 2012
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Cascade [4 + 1] annulation via more environmentally friendly nitrogen ylides in water: synthesis of bicyclic and tricyclic fused dihydrofurans

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Abstract

A novel imidazolium ylide activated [4 + 1] annulation approach is described for the diastereoselective synthesis of bicyclic and tricyclic fused dihydrofurans in water. This cascade annulation presumably proceeds via a Michael reaction triggered zwitterion enolate followed by concomitant intramolecular cyclization. The methodology has distinction of being the first report on imidazolium ylide mediated [4 + 1] annulation in water as a unified greener approach involving an in situ base regeneration system and an alternative to pyridine ylide.

Graphical abstract: Cascade [4 + 1] annulation via more environmentally friendly nitrogen ylides in water: synthesis of bicyclic and tricyclic fused dihydrofurans

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Publication details

The article was received on 12 Aug 2012, accepted on 03 Oct 2012 and first published on 04 Oct 2012


Article type: Communication
DOI: 10.1039/C2GC36276G
Green Chem., 2012,14, 3269-3272

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    Cascade [4 + 1] annulation via more environmentally friendly nitrogen ylides in water: synthesis of bicyclic and tricyclic fused dihydrofurans

    A. Kumar, S. Srivastava and G. Gupta, Green Chem., 2012, 14, 3269
    DOI: 10.1039/C2GC36276G

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