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Issue 23, 2014
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Lewis acid-promoted cyclization/halogenation of allenyl ethenetricarboxylates and the corresponding amides: stereoselective synthesis of haloalkenyl five-membered heterocycles

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Abstract

Lewis acid-promoted intramolecular reactions of allenyl ethenetricarboxylates and the corresponding amides have been examined. Reactions of allenyl ethenetricarboxylates and the amides with Lewis acids such as AlCl3, AlBr3 and ZnX2 (X = Cl, Br, I) gave 3,4-trans haloalkenyl five-membered heterocycles stereoselectively. The stereochemistry was determined by NOE experiments and reduction of the cyclized products. Various transformations of the haloalkenyl functionalized cyclic compounds have also been performed.

Graphical abstract: Lewis acid-promoted cyclization/halogenation of allenyl ethenetricarboxylates and the corresponding amides: stereoselective synthesis of haloalkenyl five-membered heterocycles

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Publication details

The article was received on 30 Jan 2014, accepted on 10 Apr 2014 and first published on 11 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00233D
Citation: Org. Biomol. Chem., 2014,12, 3964-3975
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    Lewis acid-promoted cyclization/halogenation of allenyl ethenetricarboxylates and the corresponding amides: stereoselective synthesis of haloalkenyl five-membered heterocycles

    Y. Fukushima, S. Yamazaki and A. Ogawa, Org. Biomol. Chem., 2014, 12, 3964
    DOI: 10.1039/C4OB00233D

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