Jump to main content
Jump to site search


Enantioselective rearrangement of indolyl carbonates catalyzed by chiral DMAP-N-oxides

Author affiliations

Abstract

Bifunctional chiral DMAP-N-oxides have been reported for the highly enantioselective rearrangement of indolyl carbonates. Using 2.5 mol% of chiral DMAP-N-oxide, diverse oxindoles containing an all-carbon quaternary stereocenter were obtained in excellent yields (up to 98% yield) with high enantioselectivities (up to 96% ee). Compared to the widespread use of chiral DMAP and isothiourea catalysts, in which the nitrogen atom serves as a nucleophilic site, we found that chiral DMAP-N-oxides, which utilize the oxygen atom as a nucleophilic site, were also efficient organocatalysts in this rearrangement.

Graphical abstract: Enantioselective rearrangement of indolyl carbonates catalyzed by chiral DMAP-N-oxides

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Sep 2019, accepted on 11 Oct 2019 and first published on 12 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01146C
Org. Chem. Front., 2019, Advance Article

  •   Request permissions

    Enantioselective rearrangement of indolyl carbonates catalyzed by chiral DMAP-N-oxides

    M. Shan, T. Liang, Y. Zhang, M. Xie, G. Qu and H. Guo, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01146C

Search articles by author

Spotlight

Advertisements