Jump to main content
Jump to site search

Issue 13, 2017
Previous Article Next Article

Organocatalytic diastereoselective synthesis of spirooxindoles via [3+2] cycloadditions of azomethine ylides with α,β-unsaturated esters

Author affiliations

Abstract

An efficient three-component organocatalytic cascade 1,3-dipolar cycloaddition reaction of in situ generated azomethine ylides with α,β-unsaturated esters is described. This reaction afforded a small library comprised of 20 new highly substituted spirooxindole derivatives. The products were obtained in yields up to 76%, usually as single diastereomers. A range of different hydrogen bond donor, Brønsted basic or acidic organocatalysts were tested. Bifunctional thioureas and squaramides were identified as competent catalysts for this transformation. The effect of microwave irradiation, as well as solvent-free conditions, was also examined.

Graphical abstract: Organocatalytic diastereoselective synthesis of spirooxindoles via [3+2] cycloadditions of azomethine ylides with α,β-unsaturated esters

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Jan 2017, accepted on 16 May 2017 and first published on 02 Jun 2017


Article type: Paper
DOI: 10.1039/C7NJ00189D
Citation: New J. Chem., 2017,41, 5506-5512
  •   Request permissions

    Organocatalytic diastereoselective synthesis of spirooxindoles via [3+2] cycloadditions of azomethine ylides with α,β-unsaturated esters

    T. Peňaška, K. Ormandyová, M. Mečiarová, J. Filo and R. Šebesta, New J. Chem., 2017, 41, 5506
    DOI: 10.1039/C7NJ00189D

Search articles by author

Spotlight

Advertisements