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Pd-Catalyzed carboannulation of γ,δ-alkenyl oximes: efficient access to 5-membered cyclic nitrones and dihydroazines

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Abstract

We report that the Pd0-catalyzed carboannulation of γ,δ-alkenyl oximes with aryl and vinyl halides offers a straightforward entry path to 5-membered cyclic nitrones or 6-membered cyclic oxime ethers, wherein substrate conformation can result in divergent reactivity, a phenomenon that likely arises from a shift in the mechanistic paradigm. The title transformation features a catalyst-controlled bond formation event that holds promise for the enantioselective synthesis of these important heterocycles.

Graphical abstract: Pd-Catalyzed carboannulation of γ,δ-alkenyl oximes: efficient access to 5-membered cyclic nitrones and dihydroazines

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Publication details

The article was received on 07 Oct 2018, accepted on 13 Dec 2018 and first published on 18 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01076E
Citation: Org. Chem. Front., 2019, Advance Article
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    Pd-Catalyzed carboannulation of γ,δ-alkenyl oximes: efficient access to 5-membered cyclic nitrones and dihydroazines

    B. Sun, S. Liu, M. Zhang, J. Zhao and Q. Zhang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01076E

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