Issue 7, 2014

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
28 Apr 2014
Accepted
29 May 2014
First published
30 May 2014

Org. Chem. Front., 2014,1, 742-747

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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