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Enantioselective Rearrangement of Indolyl Carbonates Catalyzed by Chiral DMAP-N-oxides

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) and high enantioselectivities (up to 96% ee). Compared to the widespread use of chiral DMAP and isothiourea catalysts, in which the nitrogen atom serves as the nucleophilic site, we found that chiral DMAP-N-oxides, that utilize the oxygen atom as the nucleophilic site, were also efficient organocatalysts in this rearrangement.

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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, Accepted Manuscript

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    Enantioselective Rearrangement of Indolyl Carbonates Catalyzed by Chiral DMAP-N-oxides

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

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