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Issue 4, 2018
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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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Article information


Submitted
18 Oct 2017
Accepted
13 Nov 2017
First published
14 Nov 2017

Org. Chem. Front., 2018,5, 640-647
Article type
Research Article

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, 5, 640
DOI: 10.1039/C7QO00948H

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