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Phosphine catalyzed δ-carbon addition and isomerization of alkynones to ketimines: the preparation of 1,3-diene substituted dihydroquinazolinones and 3-aminooxindoles

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Abstract

In this paper, we disclosed that alkynones could be activated as nucleophilic synthons of dienes to smoothly react with several ketimines upon phosphine catalysis, providing three kinds of α-amino diene derivatives in moderate to excellent yields. A plausible mechanism has been proposed on the basis of control experiments. Transformations of 3,5-dien-2-one derivatives were also performed to provide diverse polyene products.

Graphical abstract: Phosphine catalyzed δ-carbon addition and isomerization of alkynones to ketimines: the preparation of 1,3-diene substituted dihydroquinazolinones and 3-aminooxindoles

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Publication details

The article was received on 29 Aug 2017, accepted on 27 Sep 2017 and first published on 28 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00772H
Citation: Org. Chem. Front., 2017, Advance Article
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    Phosphine catalyzed δ-carbon addition and isomerization of alkynones to ketimines: the preparation of 1,3-diene substituted dihydroquinazolinones and 3-aminooxindoles

    Y. Sun, Y. Wei and M. Shi, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00772H

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