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Issue 1, 2012
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Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information

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Abstract

Indolizinones are under-explored N-heterocycles that react with exquisite chemo- and stereoselectivity. An exploration of the fundamental reactivity of these azabicycles demonstrates the potential to relay stereochemical information from the ring-fusion to newly formed stereocenters on the bicyclic core. The indolizinone diene undergoes selective hydrogenation and readily participates in Diels–Alder cycloadditions as well as ene reactions. The vinylogous amide embedded in the five-membered ring is resistant to reaction when the diene is in place. However, removal of the diene allows for diastereoselective hydrogenation of, and 1,4-additions to, the vinylogous amide. These fundamental reactions with indolizinones have provided a structurally diverse array of products that hold promise in the context of natural product synthesis.

Graphical abstract: Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information

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Publication details

The article was received on 19 Aug 2011, accepted on 20 Sep 2011 and first published on 20 Sep 2011


Article type: Paper
DOI: 10.1039/C1OB06423A
Citation: Org. Biomol. Chem., 2012,10, 70-78
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    Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information

    A. R. Hardin Narayan and R. Sarpong, Org. Biomol. Chem., 2012, 10, 70
    DOI: 10.1039/C1OB06423A

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