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A diversity-oriented synthesis of cyclopenta[b]pyrroles and related compounds through a calcium(II)/copper(II) catalytic sequence

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Abstract

We report herein a sequential bicatalytic route to provide a versatile access to a wide range of synthetically useful nitrogen-containing heterocycles in a single pot from furan and aniline derivatives. This transformation relies on an aza-Piancatelli/hydroamination sequence promoted by common calcium(II) and copper(II) salts. Depending on the substitution pattern of the precursors as well as the solvent employed, this method enables the preparation of biologically relevant molecules such as cyclopenta[b]pyrroles, pyrrolo[1,2-a]quinoxalines and also a novel class of cyclopenta[b]pyrrolines. Moreover, the first atropodiastereoselective synthesis of N-aryl cyclopenta[b]pyrroles is described.

Graphical abstract: A diversity-oriented synthesis of cyclopenta[b]pyrroles and related compounds through a calcium(ii)/copper(ii) catalytic sequence

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Publication details

The article was received on 18 Oct 2017, accepted on 13 Nov 2017 and first published on 14 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00948H
Citation: Org. Chem. Front., 2018, Advance Article
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    A diversity-oriented synthesis of cyclopenta[b]pyrroles and related compounds through a calcium(II)/copper(II) catalytic sequence

    L. Marin, R. Guillot, V. Gandon, E. Schulz and D. Lebœuf, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00948H

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