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Issue 9, 2015
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Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(ii)–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines

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Abstract

Catalytic decomposition of diazomalonates and other diazoesters using Rh(II)- and Cu(II)-complexes in the presence of α,β-unsaturated δ-(N-aryl)amino esters gives rise to the formation of multi-functionalized pyrrolidines with yields of up to 82%. The reaction apparently occurs as a domino process involving the initial N-ylide formation followed by intramolecular Michael addition to the conjugated system of amino esters to afford the pyrrolidine heterocycle. The whole process can also be classified as a [4 + 1]-annulation of the δ-amino α,β-unsaturated ester with the carbenoid intermediate.

Graphical abstract: Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(ii)–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines

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Article information


Submitted
21 Nov 2014
Accepted
22 Dec 2014
First published
13 Jan 2015

Org. Biomol. Chem., 2015,13, 2640-2651
Article type
Paper
Author version available

Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(II)–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines

J. J. Medvedev, O. S. Galkina, A. A. Klinkova, D. S. Giera, L. Hennig, C. Schneider and V. A. Nikolaev, Org. Biomol. Chem., 2015, 13, 2640
DOI: 10.1039/C4OB02454K

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