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Issue 2, 2019
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N-Heterocyclic carbene catalyzed chemo- and enantioselective cross-benzoin reaction of aldehydes with isatins

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Abstract

A highly chemoselective intermolecular cross-benzoin reaction of aldehydes with isatins enabled by asymmetric N-heterocyclic carbene (NHC) catalysis is described, and it provides 3-substituted-3-hydroxyoxindoles in moderate to good yields with moderate to excellent enantioselectivities. This reaction can be readily scaled up, the products could be straightforwardly reduced to the corresponding 1,2-diols, and the trityl (Trt) protecting group could be easily removed without erosion of enantioselectivities.

Graphical abstract: N-Heterocyclic carbene catalyzed chemo- and enantioselective cross-benzoin reaction of aldehydes with isatins

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Publication details

The article was received on 10 Oct 2018, accepted on 21 Nov 2018 and first published on 22 Nov 2018


Article type: Research Article
DOI: 10.1039/C8QO01085D
Citation: Org. Chem. Front., 2019,6, 172-176

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    N-Heterocyclic carbene catalyzed chemo- and enantioselective cross-benzoin reaction of aldehydes with isatins

    J. Xu, J. Peng, C. He and H. Ren, Org. Chem. Front., 2019, 6, 172
    DOI: 10.1039/C8QO01085D

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