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Issue 7, 2014
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Highly stereoselective construction of adjacent tetrasubstituted carbon stereogenic centres via an organocatalytic Mukaiyama-aldol reaction of monofluorinated silyl enol ethers to isatins

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Abstract

We report the first organocatalytic activation of monofluorinated silyl enol ethers 1, by nucleophilic tertiary amine catalysis, to develop asymmetric reactions for the construction of fully substituted chiral carbons featuring a C–F bond. Accordingly, a highly stereoselective Mukaiyama-aldol reaction of isatins to furnish hydroxyoxindoles bearing two adjacent tetrasubstituted carbon stereocenters is developed.

Graphical abstract: Highly stereoselective construction of adjacent tetrasubstituted carbon stereogenic centres via an organocatalytic Mukaiyama-aldol reaction of monofluorinated silyl enol ethers to isatins

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Publication details

The article was received on 28 Apr 2014, accepted on 29 May 2014 and first published on 30 May 2014


Article type: Research Article
DOI: 10.1039/C4QO00126E
Org. Chem. Front., 2014,1, 742-747

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    Highly stereoselective construction of adjacent tetrasubstituted carbon stereogenic centres via an organocatalytic Mukaiyama-aldol reaction of monofluorinated silyl enol ethers to isatins

    Y. Liu, F. Liao, Y. Niu, X. Zhao and J. Zhou, Org. Chem. Front., 2014, 1, 742
    DOI: 10.1039/C4QO00126E

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