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Issue 4, 2018
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Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

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Abstract

The aldol reaction using aldehyde-derived silyl enolates as nucleophiles with aromatic aldehydes chemoselectively proceeded in the presence of silyl triflate and 2,2′-bipyridyl to produce β-siloxy aldehydes, while the aliphatic aldehydes were completely recovered. The unprecedented chemoselectivities depend on the reactivities of the pyridinium-type intermediates derived from the aromatic and aliphatic aldehydes.

Graphical abstract: Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

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Publication details

The article was received on 21 Nov 2017, accepted on 06 Dec 2017 and first published on 06 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC08936H
Citation: Chem. Commun., 2018,54, 374-377
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    Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

    T. Kawajiri, R. Ohta, H. Fujioka, H. Sajiki and Y. Sawama, Chem. Commun., 2018, 54, 374
    DOI: 10.1039/C7CC08936H

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