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Oxidative cross-dehydrogenative [2 + 3] annulation of α-amino ketones with α-keto esters: concise synthesis of clausenamide analogues

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Abstract

A one-pot oxidative cross-dehydrogenative [2 + 3] annulation of α-amino ketones with α-keto esters at room temperature is reported. The protocol features copper/organo cooperative catalysis and provides densely functionalized pyrrolones in high yields. Subsequent reduction furnished multi-substituted pyrrolidinones which represent the core-structure of the natural product clausenamide, a lead molecule for the treatment of Alzheimer's disease.

Graphical abstract: Oxidative cross-dehydrogenative [2 + 3] annulation of α-amino ketones with α-keto esters: concise synthesis of clausenamide analogues

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Publication details

The article was received on 23 Sep 2018, accepted on 30 Oct 2018 and first published on 30 Oct 2018


Article type: Communication
DOI: 10.1039/C8OB02369G
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Oxidative cross-dehydrogenative [2 + 3] annulation of α-amino ketones with α-keto esters: concise synthesis of clausenamide analogues

    V. Bhajammanavar, S. Mallik and M. Baidya, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02369G

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