Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers. Issue 4 (15th December 2017)

• Record Type: Journal Article
• Authors: Kawajiri, Takahiro; Ohta, Reiya; Fujioka, Hiromichi; Sajiki, Hironao; Sawama, Yoshinari
• Is Part Of: Chemical communications. Volume 54:Issue 4(2018)
• Page Start: 374
• Page End: 377
• Publication Date: 2017-12-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc08936h
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Unprecedented chemoselectivity between aromatic and aliphatic aldehydes has been achieved in the Mukaiyama aldol reaction using 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.