Issue 4, 2018

Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

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

Supplementary files

Article information

Article type
Communication
Submitted
21 Nov 2017
Accepted
06 Dec 2017
First published
06 Dec 2017

Chem. Commun., 2018,54, 374-377

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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