Jump to main content
Jump to site search

Issue 46, 2016
Previous Article Next Article

Breaking aziridines to construct morpholines with a gold(i)-catalyzed tandem ring-opening and cycloisomerization reaction

Author affiliations

Abstract

A convenient synthetic method for the construction of morpholine derivatives from easily available aziridines and propargyl alcohols has been successfully developed. A tandem nucleophilic ring-opening of aziridine/6-exo-dig cyclization/double bond isomerization sequence was achieved by using a single gold(I) catalyst under mild conditions. The gold(I) catalyst served as a π acid and also a σ acid to realize the dual activation of both reactants in this reaction. The obtained unsaturated morpholine products could be easily hydrogenated to achieve target morpholine derivatives with good diastereoselectivities in high yields.

Graphical abstract: Breaking aziridines to construct morpholines with a gold(i)-catalyzed tandem ring-opening and cycloisomerization reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Oct 2016, accepted on 27 Oct 2016 and first published on 27 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB02284G
Org. Biomol. Chem., 2016,14, 10973-10980

  •   Request permissions

    Breaking aziridines to construct morpholines with a gold(I)-catalyzed tandem ring-opening and cycloisomerization reaction

    S. Zhang, C. Shan, S. Zhang, L. Yuan, J. Wang, C. Tung, L. Xing and Z. Xu, Org. Biomol. Chem., 2016, 14, 10973
    DOI: 10.1039/C6OB02284G

Search articles by author

Spotlight

Advertisements