Issue 7, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
23 sept. 2018
Accepted
30 oct. 2018
First published
30 oct. 2018

Org. Biomol. Chem., 2019,17, 1740-1743

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., 2019, 17, 1740 DOI: 10.1039/C8OB02369G

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