Jump to main content
Jump to site search

Issue 9, 2015
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 21 Nov 2014, accepted on 22 Dec 2014 and first published on 13 Jan 2015


Article type: Paper
DOI: 10.1039/C4OB02454K
Author version
available:
Download author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 2640-2651
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements