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Aromatic Aldehyde-Selective Aldol Addition with Aldehyde-Derived Silyl Enol Ethers

Abstract

The Mukaiyama aldol reaction using aldehyde-derived silyl enol ethers as nucleophiles with aromatic aldehydes chemoselectively proceeded in the presence of silyl triflate and 2,2’-bipyridyl to produce β-siloxy aldehyde derivatives in high yields, while the aliphatic aldehydes were completely recovered. The unprecedented chemoselectivities depend on the reactivities of the pyridinium-type salt intermediates derived from the aromatic and aliphatic aldehydes. Namely, the pyridinium-type salts originated from the aromatic aldehydes, silyl triflate and 2,2’-bipyridyl that could react with silyl enol ethers to form other pyridinium-type salts derived from the aliphatic aldehydes, which were worked up with H2O to give the desired β-siloxy aldehydes without problematic over-reactions such as dehydration and further additions.

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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., 2017, Accepted Manuscript
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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., 2017, Accepted Manuscript , DOI: 10.1039/C7CC08936H

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